Privilege Blog

Naturalizer Shoes Thanks You For Your Support

As you may remember, I entered a style challenge. And then won. I’m still chuckling and shaking my head quickly side to to side. Next thing you know I’ll start with the folksy comments about pigs flying.

But we’ve got shoes to give away here! Two of you will win a pair, from among the 13 below, if you do the following:

  1. Comment. Tell me a story about the most uncomfortable shoes you ever had.
  2. That’s it.

These four are my favorites. A little equestrienne, AKA the Jersey,

Naturalizer Jersey - Banana Bread


ladylike, in the Applause, (love the tortoise detail but if you want to you can call it leopard),

Naturalizer Applause - Blacka motorcycle variant, the Britain, (why do the British get to claim the moto boots, one wonders, briefly),

Naturalizer Britain - Taupe


and just sexy enough that even the sexy-avoidant might give them a go. Known as the Carmen. We’ll pretend it’s an opera where nobody dies.Naturalizer Carmen - Berry Red

 But there are 9 other pairs to choose from. Everybody gets to have their own favorites, as I am not yet the boss of the world. There’s the Paisley.

Naturalizer Paisley - Classic NavyThe Paitlyn (this name I simply cannot absorb, sorry, guys). Naturalizer Paitlyn - Antiba Green The Salene, Naturalizer Salene - Multi Brown the Lamont, Naturalizer Lamont - Black

the Kassandra (in a rather luscious purple, can I change my mind about favorites?)Naturalizer Kassandra - Grape the Lecture, Naturalizer Lecture - Teal Black the Lucille, Naturalizer Lucille - Black the Napina, Naturalizer Napina - Black and finally, the Nation.Naturalizer Shoes

I’ll announce the winner on Monday.

I suppose I thank you so often that it gets a little old. But that’s not going to stop me from doing it again. Thanks.

By the way, there’s a Flash Sale today. Remember how you Liked their page? Now that will get you access to really, really, really low prices:):


148 Responses

  1. I’m upset as I think about this, but my worst case of foot rage occurred on the day my son was married. This is not how I envisioned myself, all teary-eyed from pain. My mask was the tears of happiness for my newlyweds. Thankfully I relented when the Salsa started, and off they came.

    Every now and then I still look at those beauties sitting innocently in my closet, and remember with joy and agony, their one day of glory.

  2. Love your generosity with the give-aways, you always come across as a very giving person in your approach to many areas of life.

    And on another topic, since Pinterest has decided to ‘give’ me scads of ‘unrelated pins’, I have sadly decided to unfollow all boards, including yours :-( Don’t have the time to waste on trying to find the gold in all this dross. Thought you might like to know.

  3. A pair of very stylish sandals I brought on one of my first business trips. In fact, they were the only pair of shoes I brought besides running shoes. Chicago in July, lots of standing and city walking. I can’t describe how painful the blisters were. Young and dumb, I cared more about wearing cute shoes then buying a pair of comfortable ones!

  4. Ah, those would be the sandals whose straps rubbed so badly that I had to stick moleskin strips on them, and they were still uncomfortable. ugh! A comfortable pair of shoes is a true delight.

  5. From the time I was 18 (and fell off a horse, broke my foot, had tons of stitches and ended up with an enormous bunion from scar tissue) until I was 40 and FINALLY had that bunion removed- all shoes were painful. Why did I wait so long?? No idea.
    But almost 18 years post surgery I am reveling in shoes….where shoes before were just something on my feet to protect them from hot pavement…now they are a joy.
    Add to the mix two teenage daughters -Miracles! we all wear the same size- and shoes are, dare I say, fun!?
    Still not wearing the sky high heels but boots! oooo. I love boots! And kitten heels when I can find them. And flats. Even flip flops.
    So comfy shoes from Naturalizer- that would be a Yes, please.
    And thank you.

    1. @Nancie Bee, Butter Shoes from Baltimore designs beautiful kitten heeled shoes. Most are the typical 2″.. You can sort for the low heels. Sometimes Butter is offered through Haute Look, a division of Nordstrom, a discounted flash sale. There is a Free App. I have two pairs. I love their combo kitten heel/D’Orsay styles: many in colorful prints and suedes which make them ultra-comfortable. You can also search for kitten heel on Nordstrom’s new updated shoe dept. website. I only wear 2″ heels or less. They are easier to find than they used to be.

  6. I thought wearing a chunky-heeled funky black suede pair of mary janes would be a cute and comfortable option for a night out at a gothic-industrial-ebm club. Was I ever wrong!! The round toes were hard and pinching and my left heel broke off early in the evening. That left me trying to walk and dance all night in a very lopsided manner. Now I always make sure to have a spare pair of black ballet flats in my car.

  7. Ooooo– beautiful selection!

    I had a gorgeous pair of blue silk booties when I was 17. The heels weren’t terribly high, but because of the angle of the shoe, anytime I had to stand in them for more than a couple of minutes my feet would fall asleep. They were completely numb. It was wildly uncomfortable, but I wore those shoes until the heels fell off!

  8. i had a pair of knee-high lace-up combat boots with 12″ custom platform heels that i would wear to walk around the stanford campus at dusk; it was an act of athleticism to stride around in them, but it was absolutely worth it for the double-takes i’d get when people saw my nearly-seven-foot silhouette in the gloaming.

    halfway through the annual eurotrash party at the maison française one year i decided to sneak up to my room and change into the boots; as i was already wearing a kelly green wig and a black plastic dress, when i rejoined the crowd, i was promptly mistaken for a drag queen. that was, one could argue, the most uncomfortable i’ve been in shoes.

  9. My most memorable shoe pain happened when I was mother of the bride. It detracted so much from my enjoyment of the day! I never wore the shoes again. I always wear comfortable shoes now, at least shoes that promise to be comfortable when I purchase them. I’m on a limited budget, it’s worth it to spend a little more for comfort. Pricey doesn’t always mean comfy, though.

  10. my wedding… very cute turquoise kitten heels, went really nicely with my artist-made head piece, but after serious dancing, we went back to the hotel barefoot..somehow I seem to remember that moment clearer than the rest of that night…!

  11. There were too many uncomfortable shoes to choose from! The most recent was a pair of Dansko shoes that I’ve since donated. The tag/logo was inset in the heel of the insole and gave me a blister on the sole of my foot every time I wore them.

  12. Love the boots at the top! I have twice bought really cute heels that were a little too small and oh the agony! As if them being tall wasn’t bad enough, slightly misjudging the size as well is the worst (and so easily done if your feet are cold when you try them on etc etc).

  13. I love those moto boots. My least comfortable shoes were my wedding shoes. I spent photos and the reception teetering around at almost 6′ to be closer to David’s 6’4″ and kicked them off in the car on my way to the reception. I spent my reception running around barefoot through the barn and farm. Those gold heels haven’t been touched since.

  14. As a poor college freshman, I had to have a pair of the wooden Dr. Scholl’s sandals that all the sorority girls wore. They absolutely shredded my feet, but I foolishly persevered wearing them for weeks. Wearing cool shoes was more important than maintaining the ability to walk. But things have changed.

  15. The Saline is calling my name!
    Here is my story: I once spent 4 hours hiking the Sierras in a very unsuitable pair of lightweight tennis shoes (similar to Keds). At the end of the day I had large fluid filled blisters on the soles of both feet. I literally couldn’t walk for days. It’s not really the fault of the sneaks, but certainly my most uncomfortable experience in shoes!

  16. A pair of shoes I wore as a bridesmaid. I was very happy I had brought a pair of dancing shoes in their stead!

  17. I had a pair of sexy black leather pumps that I wore to a symposium that I was speaking at. I guess they were a little too high, a little too sparse in the cushioning, and we had to walk a little too fair across icy sidewalks. I ended up with a really bad case of metatarsalgia, and had to get a padded boot and crutches for a week.

  18. And thank you right back for your generosity, as always!

    The most uncomfortable shoes I can recall (mind you, I have given ‘uncomfortable’ up for the duration of my days) were a pair of ballet pink high heels….that were at least 4 inches high and had leather ties that wrapped around the ankle. Not only were the balls of my feet in shreds, but the ankle…..calling the aftermath ‘lacerations’ would not be an exaggeration. I have no idea what I was thinking. Those boots look gorgeous–and comfortable!

  19. I have a pair of sandals that cause blisters every time I wear them. I see them in my closet every now and then and think to myself, “Why don’t I wear these more often?” Ten minutes after I put them on, I’m reminded why.

  20. I have always worn well made shoes, with a heel. When reaching 50, I decided to see what all the ‘comfort fuss’ was about and bought myself some handmade sheepskin slippers. They were exquisite, soft and flat and I was enthralled. I wore them almost non-stop for a week, whereupon I developed plantar fasciitis which has troubled me for the last eighteen months. Apparently, my shape of foot is built for heels…and I am now healed sufficiently to go on the search for a new pair. Happy days!

  21. My favourite shoes were purple flats with a gross grain ribbon bow on the toe…they were suede. I wore them during my surgically induced full throttle menopause when I was feeling blue. If I wasn’t gourging myself in chocolate I was wearing my purple shoes….they took me to museums, movies, to street cafés, to work, to the theatre with Mother on Saturdays. I put so much mileage on these I wore them out…it was a very sad day when I had to retire them and I have never felt the same attachment to any shoe, before or since.
    I think they were Ferragamo’s bought second hand in size 6 1/2…

    Thank you for hosting another great giveaway Lisa.

  22. Remember them well. Peep toe pumps. Black patent. NOT cheap shoes, but dreadfully uncomfortable! One contributing factor: extra heel height. We sturdy girls just don’t do uber high heels. Another problem: very narrow toe box. My little piggies didn’t enjoy being squeezed! Will never know what possessed me to purchase the shoes in the first place.

  23. An adorable pair of platformed suede booties. Ordered online and not properly auditioned before wearing them out. Fast forward to mid-evening and I’m hating them so badly I consider multiple times going barefooot, first at a dirty, sticky concert venue (Bimbos in SF), then along the (not sanitary) streets of North Beach. They went to Goodwill the next day.

  24. My mom loved the look of saddle shoes on a little girl, so I had multiple pairs growing up. Unfortunately, they were all cheap and cut under my ankle bone and on the back of my ankle. I still have more scar tissue than real skin in those spots, and still disagree with my mother on the value of good, comfortable shoes even if they cost more :)

  25. Not just uncomfortable but positively mortified. I took my son to an open day at a potential university in Manchester (UK) a city notorious for rain. Well prepared in my Mackintosh, (don’t you just love a real Mackintosh) with polka dot umbrella and comfortable black loafers, I accompanied my son across campus for a couple of hours in torrential rain. My feet were soaked through. When finally we finished I decided to treat myself to a new pair of shoes as we had a long journey home ahead of us and wet feet just didn’t cut it. Spying a beautiful pair of flats (I’m a sturdy girl through and through) in the window of a swish shop, we went in to try them on. I casually flicked off my loafers and saw a look of horror sweep across the rather haughty assistant’s face. I looked down and my feet were black, coal miner black, man of the road black, black like I’d bathed them in soot. The dye from my shoes had permanently tattooed my feet. I tried valiantly and failed miserably to laugh it off – no casual insouciance from me. Uncomfortable? I’d have given my right arm, left leg and both feet to have stumped out with a shred of dignity. Needless to say my son was hysterical – I had never seen him laugh so much. It took me almost a week of regular scrubbing to get my feet back to grey and a further week to glory in their ghostly whiteness.

  26. I can forgive shoes that hurt. Really. I can. If they are gorgeous I can be (a bit) willing to put up with their oddities. I can even like the feeling of having to hang to my man’s arm to keep me steady. What I cannot forgive is bad looking shoes that even hurt. Because then, I don’t know anymore what I am suffering for. And I discovered recently that flat, pretty plain shoes can hurt too. And that really seems too unfair to me, a big univesal injustice.

  27. Ah, shoes! A love and hate affair! Funniest was the time I bought a pair of the softest suede, most beautiful deep purple round-toe pumps at a price not to be believed. I thought they felt a little weird but I decided to keep them because of their beauty. But out with an artsy friend of mine at lunch the next day, she took one look at my feet and shrieked “OMG, what did you do to your feet?” They were both the right shoe, you see. I was blinded by the round toe – and, of course, the beautiful suede and the price tag.

  28. Not long ago I took myself back to a corporate job. After years of working from my home studio, where I was able to make a living AND raise a family, I decided to give it a go in Corporate America at age 50+. I came in at a sort of low level, in an attempt to get my skills up a notch. I bought myself some very fancy shoes with VERY high heels. Seemed like a good idea at the time. All I had to do was get myself from my car, to the elevator. Imagine a company filled with fashion forward 28 year olds. The company was located at the tippy top of a highrise. Every day I would put on my fancy shoes and take the elevator up, up, up and then if I could just make it to my chair, I was golden. I was golden UNTIL the day the fire alarm went off. We had to take the stairs down. DOWN. DOWN. DOWN. It was a LONG way down. My feet were raw. I discreetly found the corporate medicine cabinet, patched myself up and went back to work! Next day I came in flats.

  29. My most uncomfortable shoes were the green glittery flats I bought for my undergraduate graduation. They were so stiff that by the time we were heading to the ceremony my feet were covered in cuts and blisters. My mum ended up running to the chemist to get stuff to bandage up my feet. As soon as the ceremony finished I spent the rest of the day walking round in bare feet.

  30. In my youth I wore a lot of uncomfortable shoes, always convincing myself that it wouldn’t be that bad, and if it was I’d just have an extra drink and tough it out. I had a gorgeous pair of black stilettos I bought for a special event that lived in the back of my closet. I’d pull them out for a party, wear them, end up near tears or worse, barefoot, and remember why they lived in the back of my closet. Months later, the cycle would repeat. Honestly, they were probably too small, as I’d have to spend some time stretching my feet before I could even walk properly without them. I finally attended a wedding where the hosts provided a basket of sandals so ladies who wanted to kick off their heels wouldn’t go barefoot. I switched my shoes as soon as the dancing started, and left the heels under the my table at the reception. Thankfully, I forgot to pick up the shoes at the end of the night, and was not sad when I recalled my error. That was the night I resolved to stop buying painful “pretty” shoes…because no one looks pretty while wincing from foot pain.

  31. I have ridiculously sensitive feet and a low tolerance for avoidable pain so while I have a lot of uncomfortable shoes stories most of them are very short because I try to be careful about getting rid of them as soon as possible.

    But, having fallen in love with a gorgeous pair of patent, leopard Ferragamos flats, and having then received them as a surprise and very sweet gift… I was really really determined to make them work. They become literally agony on my feet within five minutes, the area around the bone under the big toe completely unforgiving. I’ve worn them with socks, I’ve worn them to events where I’m going from car to restaurant to car and still been in pain, I’ve had them stretched, I’ve worn them around the house some more – they are better but to be honest they are still really painful. If it was only the money or only the sentiment or only how pretty they are I could bear to get rid of them but the combination of all three keeps me locked in in trying to make them wearable at least occasionally.

  32. Shoe discomfort isn’t just about the style or the fit – context is a whole lot of the equation. The fall day when I wore sling back, open toed pumps and I walked home from the train in a blizzard comes to mind. I also wince when I remember the trip hiking in the Alps with a pair of boots that weren’t adequately broken in. But the worst was in 1980 when I worked at a very conservative bank. I had spent the weekend at my fiance’s and had remembered to bring, suit, blouse and pantyhose for Monday morning, but I forgot to take dress shoes. I walked into the building in my running shoes. People gasped in the elevator. When my colleague saw, she told me we couldn’t have the scheduled meeting in the conference room. Instead, we’d have it in my office where I could hide my feet behind my desk. She also advised me to walk the ten flights down the fire stairs, go around the corner to a shoe store and not come back until my feet were properly attired. The salesman laughed when I walked in and I told him that never in his career would he have a surer sale.

  33. I have learned to throw truly uncomfortable shoes into the Goodwill pile as quickly as possible (better yet, don’t bring them home in the first place), so most of my truly epic shoe pain comes from wearing shoes that are perfectly fine for their intended use case (e.g., walking a short distance, being seated for an hour and a half, and returning to where I change into flats immediately) in less-than-appropriate contexts, such as hiking hither and yon for my best friend’s wedding photos. This particular example ended up with me walking barefoot (such clean streets!) and changing into my flats at my first opportunity.

    Can I take a moment to question why the gents get to sit down for photos when the ladies have just hiked the world in heels?

  34. Those flats ARE tortoise-shell — no leopard-calling allowed!

    And where did they come up with “the Lecture” as a style name? Kind of takes the fun out of it, no?

    One of my first jobs, post-college, in NYC. They were taupe Etienne Aigner peep-toe heels. I stood on one foot on the subway, alternating feet. While the pain on the standing foot was worse, the sweet relief in the lifted foot was exquisite.

  35. Well, the last uncomfortable pair was worn this last May in Paris. I was celebrating my 60th and thought I would try to look a bit stylish as we roamed around the city, but after just a few hours in my new flats I was forced to return to the apartment and put on my black sneakers, never to wear my stylish flats again. My previous job had me on my feet most of the time so whenever I was home, off came the shoes and on went the slippers. I think my feet have widened because of it, plus, aging does it also, so my pointy toed flats were a nightmare.

  36. Gorgeous tweed + leather t-strap heels. Too bad the little buckle on the strap poked/itched/stabbed/burned to high heaven.

  37. When I was 25 and still in my “cheap shoes and lots of ’em!” phase, I bought a pair of gray and blue plaid pointy toed flats from Target. They pinched my toes, I swear they caused bunions, they rubbed my heels raw and my feet never completely fit perfectly in them so I ended up kind of weirdly hobbling around whenever I wore them.

    But they were so cute and I still miss them.

  38. One New Year’s Eve, I was young enough ti buy boots just for this evening, and I decided to wear stiletto boots. I can’t remember what I had in mind, but I do remember sitting on the floor without the boots, while my feet were aching and swollen.
    I’ve learned not to buy shoes last minute before an important event, and also to trust my feet, not my eyes when choosing.

  39. My favorites are the Jersey too!

    My most uncomfortable shoes were probably Bass loafers I wore in high school before I learned how shoes ought to fit. Too tight, no socks, terribly mangled heels for ages!

  40. I wore a pair of cheap black wedges on a day traipsing around Seattle when I was checking it out as a place to live. I was limping by the time I got on the plane, and I’m almost certain I actually broke something. I still moved there, though, and spent three years living like the locals in the comfiest Birkenstocks I could find.

  41. My most uncomfortable shoes were a pair of loafers all the cool kids had. It had to be the exact brand and color. After saving up for them, they absolutely killed my feet. Blisters so bad that my feet bled so much I thought my blood would stain the leather.

    Ah what we do for social acceptance. However that was the last time I made myself wear uncomfortable shoes. I have made mistakes since, but never did I let myself suffer like that, and some of my mistakes since have been far more expensive.

  42. Gosh, the first pair, the Jersey, is absolutely gorgeous. Well done.
    Anyway, When I was younger I was always apprehensive getting new shoes because I always got blisters. But nothing could compare to a pair of shoes I persuaded my mum to get for me. They were similar to the Applause and I thought they were really grown up. I wanted to be grown up and I would wear them but oh it would hurt. The thing is, my feet are wide and I cannot wear narrow shoes. And those really were very narrow flats. But i didn’t know that then so I suffered until I could stand it no longer and gave up on growing up for a while.

  43. Walking around Brooklyn, I knew enough to wear comfortable shoes. Flat and soft, I felt pretty good in those loafers. Unfortunately they were a little too soft, giving me no support whatsoever. While crossing a busy street, my ankle turned in them and I fell forward. After assuring everyone that the only thing I hurt was my pride, I got up and threw the shoes away once we got back to our room. The uncomfortable part was that I fell in front of a bus, knocking down one of my daughters in the process!

  44. In a fit if insanity, I purchased the cutest pair of kitten heeled, Prada, pointy toed sling backs with a sweet bow on the front. You would have thought there were little angry Italians inside the toes, pinching my feet. I wore them twice, then set them free.

  45. I think the most uncomfortable shoe I’ve ever had is the boot I’m currently wearing thanks to my ortho. surgeon. It is driving all other painful shoe memories away!

  46. the most uncomfortable pair of shes i’ve ever owned are essentially every pair of shoes i’ve ever owned (that are not worn with thick boot/wool/athletic socks).

    i suspect that my heels are made of tissue paper, because every pair of shoes digs and scrapes and cuts them up until they are bloody and raw and look like hamburger meat! gross visual, but i cannot fathom why every pair of shoes i own does that (and note i’ve tried varying the fabric, cut, and size often enough to establish that those factors have no effect). one would think i would have developed a thick amount of scar tissue back there – one would be wrong!

  47. I just wanted some black ballet flats. This pair felt just a tiny bit tight, and I foolishly believed that they would stretch enough–leather stretches, right?–to fit around my bunions. I was wrong.

  48. When I was young I also sacrificed comfort for looks… I had a beautiful pair of patent leather pumps with absolutely no give in the soles… It was pure punishment beating the pavement in those things but man I looked good! Nowadays I have no love for the flip-flop (we used to call them “thongs” long ago). How can people wear them anywhere but poolside? No support, no protection, and the bit that goes between the toes chafes!

  49. I refuse to travel with anything more than a carry-on and a small back-pack and I won’t wear running shoes on a plane. So, when I got the company memo about bringing athletic shoes to the corporate meeting in S.F., I dismissed it- I just had no room in my luggage. I couldn’t see what the problem would be; after all, I’ve run full tilt through airports in heels.
    I wore my a little bit too tight but oh so stylish grey Mary Jane heels along with my jeans to the team event. Not quite what I bargained for. It was a race. A scavenger hunt/race through the hills of San Francisco. From Union Square through Chinatown, up to Coit Tower, across the City to Cow Hollow and finally to the Marina. My team was mostly guys – young guys – and I was a woman in my mid-50s. I uttered not a word of complaint and dashed up and down the steepest streets in concert with them. By the time we returned to the hotel, my feet were bleeding. That, of course, impressed the guys even more. I still have the shoes, but now, when I slip them on for a night out, they end up tossed in the corner before I even make it to the front door. Here’s to comfort!

  50. I remember the time I bought new shoes just before we went to Las Vegas for five days. Because we were taking only carry-on, I brought just the one pair of shoes, which I thought were quite comfortable. Within two hours of walking along the Strip they became excruciatingly painful, raising blisters. We took a cab to the outlet mall and I bought a pair of incredibly ugly “walking” shoes. With the help of bandaids and moleskin I was able to walk the rest of the trip, but I donated both pairs as soon as we got home!

  51. Many years ago, I had the pleasure of walking with the late author and illustrator, Tasha Tudor. She could see I had taken great care to dress in period costume for an event I was hosting for her, but as attentive to detail as she was, she could read the discomfort of my feet in my face. “Take off your shoes”, she advised and we both continued along barefoot to our destination. That’s my story and to this day, I walk in comfort or go barefoot!

  52. Back in my 20s, a poor student in Paris, I splurged on a pair of beautiful, trendy high-heeled cadet blue suede platform sandals. They matched a blue maxi skirt I found at the Rodier outlet and paired with a pretty floral print blouse from the Cacharel outlet. A pal and I got all dressed up and set off for a gallery opening somewhere out in a suburb called Clamart that we weren’t exactly sure how to find (this was pre-Internet, let alone HopStop). A long trek on the commuter line left us in the middle of pitch-dark nowhere, with a long way to walk–make that hobble. The soles of my feet, the front of my distended ankles, the spots where the seams rubbed, all were agony. Then of course it started to rain. I don’t remember how we got back, but those shoes were history. (We never did find the gallery)

  53. The pair I remember most was a pair of red/white/blue 2 inch heels. My toes were so scrunched into the toes (and the shoes were the correct size) that I wasn’t sure I would be able to separate my toes when I took the shoes off after standing & watching my college homecoming parade. I NEVER touched those shoes again!

    What a great give-away! Thanks for the opportunity!

  54. I was 16 when I spent all my part-time job money on a pair of sling-back blue heels. My mother hated them because they were in her words, completely impractical. I didn’t care that they hurt my feet. I loved wearing them with my mini skirt. Her sister came to our house for Thanksgiving that year. I was wearing my heels and the first thing she did was compliment me on my shoes and how adorable they were.. thank goodness for aunts!

  55. Worst shoes I ever wore were a pair of Joan & David pumps I bought at an outlet mall when I was in college. They were super-expensive for me at the time–$98–and totally beautiful. I was young and foolish enough to wear them to class trip to NYC to the opera. There was a lot of walking involved, and then a lot of sitting, and then more walking. It was a really unfortunate shoe choice. I never wore those shoes again.

    Come to think of it, I think I was wearing uncomfortable underwear that day too. So glad I’m not 20 anymore. Experience is a great thing. At least after it’s over.

  56. I have had many, many painful shoe experiences and have given away or thrown away or just left the shoes/boots in hotel rooms/trash cans in many cities in the US and in Paris (Paris got at least 4 pairs!).

    But the most painful experience was in college. I was a sophomore at the University of Texas (Austin). Wedges were in style and I rocked an awesome pair. After a night of fun, walking home from a basketball game, I slipped/fell off a curb at just the right angle to cause a fracture in my foot. With my friend’s help, I made it back to the dorm, soaked my foot in hot water during the night, but found myself at the Student health center the next day. After an x-ray determined that there was a fracture, my foot was put in a soft cast and I was handed a pair of crutches. No weight on that foot for at least 4 weeks!! If anyone has visited the UT campus, you know that it is huge. This was pre-backpack days so it was a challenge to carry, in some form or fashion ,a huge stack of books through the massive student crowds at class changes. Fortunately, some really nice guys would help but it was difficult to maintain any “cuteness” from the effort to maneuver through the heat, in the crowds, from one end of the campus to the other. The worst part of this shoe experience, though, was in my chemistry lab. I had to take my project sample to the weighing scale in the hallway. I shoved my glass jar in my pants pocket (pants were already kind of tight) and as I was trying to get to the weigh station, the jar popped out of my pocket, shot across the room and hit the floor. I can’t remember the compound we were making (nothing hazardous, of course), but the classroom was evacuated while the mess was cleaned up. Needless to say, I got an F on that project due to lack of completion.

  57. A pair of taupe Etienne Aigner (is it the color? I saw sisty’s comment above!) boots from the mid-90s with a small heel I inherited when my grandmother moved – she had never worn them and 23-year-old me couldn’t believe my luck in a brand new pair of boots!

    Well, I soon found out why she never wore them as the toe box was about an inch narrower than my foot, a problem I’ve never had with any other shoe! I think it took two days for my feet to unfold.

  58. They were gorgeous- a pair of strappy green crocodile embossed sandals. I wore them to a friend’s open studio show in the city. Being a mom from the ‘burbs, I was feeling pretty cool in my black outfit and sexy heels. The studio was located, naturally, in a warehouse. A warehouse with stairs. A warehouse with a lot of stairs. I brought my six year old son. He thought it was really fun exploring all the open studios. Did I mention the stairs? I hobbled after that kid for hours. The straps of my shoes cut my feet until they bled. It’s hard to look cool when one is grimacing in pain, it turns out. Oh, well, I donated them. Somewhere there is a poor unsuspecting soul who will be lured by the siren song of the gorgeous green heels.

  59. Mine is a wedding story too – a beautiful one in downtown San Francisco. I had a lovely navy dress and bought some strappy sandals with very high heels to better show off my leg through the long slit.

    Unfortunately, the church was downhill from the car – a very steep downhill, and I ended up having to take my shoes off in order to walk at all (I tried walking backward, but my family shamed me… ). I arrived at the wedding with a huge run up my stockings and a big bandaid wrapped around my big toe, which had come in contact with a small piece of glass. Not the look I was going for.

    I would just love those boots…

  60. My shoes were cute lime green mules. I wore them all over Disney Land and later I developed a bad case of plantar fasciitis. I have worn sensible shoes ever since.

  61. Most painful shoes? Back in high school I didn’t realize that hot shoes automatically meant they’d be uncomfortable, so I bought two separate pairs of adorable but torturous shoes for formal events. After spending an evening barefoot on gross outdoor surfaces I swore to never again buy awfully uncomfortable shoes.

    The sad thing is, since then all my shoes are not only way more comfortable … but in hindsight those shoes were more boring than they were attractive.

  62. For my first cruise, I purchased a pair of 4″ black patent pumps for our scheduled “formal night.” I made it three doors from our stateroom before I kicked them off, padded back to our room, and put my comfy flats on. They were the most uncomfortable things EVER!

  63. The most uncomfortable pair of shoes I’ve owned were a lovely pair of Ferragamo flats. I had other shoes from the brand in a similar style, but didn’t allow for the different materials this pair was made from. The were the classic bow design, but made from a wonderful tweedy wool fabric. Sadly, I took them to the consignment store. They sold quickly–hopefully to someone who found them blissfully comfortable.

  64. Pappagallo flats, hands down.

    Not one pair, not two, but many many many, and each pair as miserable to wear as the first. But so cute! I loved going into the local “Shop For Pappagallo,” utterly transfixed the minute I’d float through the door, babysitting money for the month already spent as I was getting out of the car in the parking lot. The most punishing toebox known to girl shoes, but so cute! Any young gal who falls for shape/color first, and the fit second, will know what I’m talking about.

    The shape of the shoe was so cute, but the corresponding shape of what I did to my toes by forcing them into that toebox, well today they are anything but cute.

    I had to look hard for an eBay listing of my vintage era Pappagallo flats, but this pic is very close:

    1. @Flo, Flo, your Pappagallo flats are the spitting image of my nightmare flats I had made in Bali. Looks are deceiving, and I fell hard too.

  65. I have been unable to wear anything around my ankle, since breaking it and having a plate and 8 screws added. So, goodbye to heels and boots and high-top sneakers. So glad there are cute and comfortable shoes available.

  66. This isn’t a story at all, but I’m hopeful to win out by appealing to your sentimental side and will put this on the table.

    Pointe shoes.
    Ballerina pointe shoes.

    The perils inflicted on my poor feet by something that appears so delicate and dainty is highly unfair. But that could be said about many shoes not dependent on papier mache and ribbons for support.

  67. A pair of ribbon flats that had the most awkward soles ever. They rubbed horribly. I miss the cuteness of them but I have no idea why they were horrible to walk in.

  68. I bought a pair of LL Bean hiking shoes to take with me to Guatemala. I was going there on a media trip with The Rainforest Alliance to visit sustainable coffee farms. On the first day, we had some time in Antigua to site see while other journalists still arrived. A few of us decided to hike up a hill to get a view of the city. As I was hiking, I felt my heels begin to hurt. By the time I got back to my hotel, the shoes had torn through my socks and my skin almost down to the bone. I had to wear sturdy shoes the entire week for all of the places we were visiting and I was in total pain. I was also concerned about infection, so I took the antibiotics that had been prescribed in case I had gotten any gastrointestinal issues while I was there just in case. It was well over a month after I returned home until I could wear any shoes with a back on it. Fortunately, LL Bean allows you to return anything.

  69. I was a student in France back in the 60’s, when all my young French dorm-mates wore cute little kitten heel pointy toe shoes, while we Americans tried to look cool in tennis shoes or lofers… in vain. I bought a pair of the French heels, but the shoe was built for a different kind of foot than the American foot, and I could do nothing but hobble in them. To this day, I don’t know how they tromped the long distance to classes in those light-weight thin-soled toe-crushers. But now, even French women wear flats, albeit cute, expensive ones! And I’m still trying to find shoes I can be active in and look good in, all at the same time.

  70. Just this Monday, I wore a lovely pair of luggage tan boots with wedge heels to work. Looked terrific, but I was limping by lunchtime, and in agony by the time I got home. Aching toe kept me awake that night, so I bundled those beauties right off to the neighborhood consignment shop the next day, lest I be tempted by them again. Perhaps I’ve learned my lesson?

  71. My husband and I were staying the weekend in the city for his 40th birthday. His birthday is at the end of June so HOT. He decided he wanted to walk to where I had made reservations. OK I can handle that but not in the shoes I had taken with me to go with the dress that I brought for the occasion. I have plantar fasciitis and I also have DVT so I wear a compression garment on one leg. I wore the shoes until my feet couldn’t handle it anymore and then I walked in the city in bare feet to the restaurant. I pulled the stocking up over my foot so that I wouldn’t get that as dirty as my feet became. The compression stockings run about 95 dollars and well they are not cheap either. Let’s just say the shoes were the last time worn. Ihad to wear them in the restaurant but I told him I wasn’t walking back to where we were staying –we needed to take a taxi. I walk all the time and this was just plain painful.

  72. I fell in love with a pair of ballet flats on line. They were made for me by a custom shoemaker in Bali…I know, how extravagant. But they really weren’t any more expensive than usual.
    The color– a dreamy French Blue, with Navy toe caps. The leather–a buttery matte finish. Ooh and ah. This is a color that would work with just about anything and look amazing.
    All for me in size 40.
    They finally arrived in a beautiful canvas drawstring pouch, and I was so excited to squeeze my feet into them and rushed out the door to meet my husband for dinner.
    Walking from the car to the restaurant was agony. The shoes were too short. After wearing them for only one hour, they left my feet in pain for a week.
    Even two weeks at the shoemakers stretching bar did not work.
    I ended up giving them away to a friend, and I have never seen her wear them….

  73. A pair of Sasha suede black boots that I received as a present. I could not part with them for 9 years because they were so beautiful. Nor could I wear them because they were so uncomfortable.

  74. My experience was fairly recent.

    I splurged on a pair of beautiful high heeled tan leather booties to wear to the office.

    Although they seemed perfectly comfortable in the store, and in my own home that morning, they turned on me by lunchtime.

    By late afternoon, they had been kicked off and my throbbing sock-clad feet were hidden under the desk.

    The worst part was having to put them back on in order to hobble out to the car at the end of the day.

    I’m planning to visit the Naturalizer site to check out the “Britain” – they would fill a longstanding void in my shoe wardrobe.

  75. I bought these beautiful red, patent-leather, open-toe flats to wear with a navy blue pencil skirt and navy v-neck knit top. I thought those shoes would add just the right amount of glam. I wore them for the first time to a conference I organized. But the glam vision dissolved. By noon, I was hobbling around with toes and heels bloodied. The hotel staff found me some bandaids. I wore them once more before tossing them back to the shoe gods.

    I love your blog. Two things I’ve added to my wardrobe after being inspired by you: a uniqlo jacket and a pair of Oxford-ish shoes. Thanks for your inspirations!

    – Christine

  76. So many bad shoes have passed through my closet, but the worst by far were clear plastic jelly sandals I bought one summer in NYC back in the 80s. I remember walking around the city, in the hot humid summer weather wearing those sandals and no socks. My feet were sweating and making squishy noises and the blisters were breaking out all over my feet. I don’t remember what happened to those shoes, but I’m sure that got tossed out pretty quickly.
    I still see jelly sandals made for little girls and I shudder to think that any mother could torture her child with them.

  77. Well, paid a lot of money for those Tod’s loafers and I was going to wear them, dagnabbit! Sadly I chose to debut them during a long day at school; first class at 9am and last class at 6pm. My poor feet had blisters at the back and at the front, and the culprits were sentenced to a month in solitary confinement (in my closet) on the rack (that is, stuffed with shoe stretchers) before they saw the light of day again. Happily they did stretch but are only taken out for short excursions; the bad memory has faded but not disappeared.

  78. Worst footwear evah: new boots – designer gladly forgotten. First trip overseas: England in December 1981. World’s weather went wonky. COLD!!! Boots thinly soled; woefully inefficient for ice & snow. One pair of boot socks. Oh, the heel blisters thru the socks :( Did I mention COLD? And no insulation in the boots? Remedy for next trip in winter: Naturalizer wool-lined boots! :)

  79. As a woman of moderate means, high-end designer shoes have always been out of my reach. After years of yearning, I was over the moon when my husband agreed to a splurge. I rationalized that if I chose a conservative black pump, I would be able to wear them for years and really get my money’s worth. Although they felt a little snug, I settled for a pair of size 38 (they did not have a 39)beauties with the interlocking “C” embossed on the vamp. You guessed it! Although they were the most miserable shoes I have ever worn, I did suffer through numerous wearings until I could take no more. They ended up in their new home via Salvation Army donation. (I understand that they have a designer section in their thrift stores.) I like to imagine that they are gracing the feet of a woman who loves them just as much as I thought I would!

  80. Today. Today was the worst shoe pain. Black pumps (New York real estate heiress’ brand). I stood over and observed an employee for an unforeseen hour. The shoe pain and resulting irritability may have sttributed to harsher critique than necessary. Does one apologize to one’s employees for a bad shoe day?
    Afterthought, what did I expect the heiress to know about working all day in a pair of uncomfortable shoes?

  81. A pair of two-toned, patent leather wing tips that seemed to me the most beautiful shoes I’d ever seen at about age 10. My mom bought them for me in August before school started, and I was thrilled to wear my new school shoes in glossy black and white with my hand me down school — contrasting with all that plaid and grey wool. But By the second week of school, I had suffered so many slings and barbs from all the other kids poking fun at my shoes, that I could no longer wear them. The “clown shoes,” as they came to be known, were replaced by unobtrusive brown suede oxfords. The last time I saw the clown shoes they were caked with mud, having been consigned to the fields as my play shoes….

  82. I had this pair of seemingly-harmless ballet flats that managed to simultaneously a) rub across the tops of my toes, causing blisters; b) cut into my achilles; c) be loose enough that my feet slid around in them, so I’d end up with big blisters on the soles of my feet. They were cute enough that I wore them more than once, but not much more than that.

  83. The most uncomfortable shoes – wow, how to choose?

    Really, they were always the ones that I bought hoping to impress a boy! But one pair of burgundy, very high boots stands out. I bought them when I was a student teacher – and boy, did they look great with my “I’m a brand-new and fashionable student teacher working hard to look professional” skirts. Until my then-boyfriend was driving me home (lived out in the country), we broke down, and I had to walk a lot of miles in those way-too-high boots. It was winter in the Pacific Northwest so taking them off was not an option – the only option was to slog along in the rain unti, I was almost crying at each painful step. Finally, I knew I couldn’t go one step further. I told him and that lvoely guy actually piggy-backed me for long stretches until finally, we flagged a ride home. Poor swollen and painful feet – didn’t stop me from wearing those boots again though (ah, 20 – what did I know?)

    Thanks for the context and the good (albeit painful) memories of a very sweet guy! Didn’t marry him but we’re still friends!

  84. When I interviewed for a job I quite wanted in Boston as a senior in college, I of course wore my one “interview suite” and my one pair of (cheap, but nice looking) “interview shoes.” The shoes got me through the day, but I had several hours to kill before my flight. Since Boston is the city of walkers and I love to walk (in my standard flats), I decided to explore the city and wander in the hours that I had. I must have walked 4 or 5 hours in those cheap, feet-killing shoes due to my own stubbornness and inability to afford a cab. The blisters did not heal for a month! I remember what I saw of beautiful Boston, and that the interview went great, but oh how do I remember the pain most clearly. Lesson learned that day? Invest in one good pair of heels. “Interview heels” are one of the things you cannot be cheap about.

  85. Worst foot discomfort was finally biting the bullet and buying a very expensive pair of boots that I had saved for all through high school. Put them on the first time and it felt like my legs were encased in armor. Probably wore them twice. Someone mentioned that I looked like a Viking….still lust after them, but alas, gave them away to a friend.

  86. I love almost all of those Naturalizers! Who knew?? I have to say my feet lived a very unhappy life until Nordstrom moved to my area and I was able to find shoes in size 10.5. ( For some reason many shoe manufacturers decide that 10.5 just isn’t a good size, and skip right to 11. ) And the only place to buy “big” sizes was an awful specialty store that only stocked really horrible things.
    Now all those blisters are behind me, and I refuse to wear any shoe that isn’t truly comfortable.

  87. Can this be uncomfortable ABOUT shoes??? I have a nice pair of winter boots I bought on sale last spring. They were a little big but I thought they’d be OK. Fast forward to cold weather this year and guess what – they don’t fit any better. Imagine! I usually wear a 7-71/2 and I was thinking these are an 8, but they’re Sporto so they run small. Looked at the Giving Tree at work and spotted a tag for a girl, 15, who wanted boots, women’s size 8. Perfect! I’m going to take them in today. BUT – when I looked closely they’re a size 9 (there’s just one tiny tag inside w/size, no box). But the brand runs small and there’s no way I would think I could wear a regular size 9, so I’m positive they fit like an 8. So it’s good, right? Then I start to worry this isn’t what she meant by “boots.” What if she really wanted Ugg style boots? Or riding boots? I know, I know, if she wanted something specific she would have said so. I worry she’ll be disappointed. But they’re brand new, upper calf-knee high, black suede with furry lining that shows through the laces… they are cute. She’ll probably be thrilled. And if her mom’s around she’ll probably borrow them. Anyway, this is the most uncomfortable I’ve been ABOUT shoes in a long, long time!

  88. They are impressive…
    At my Graduation in 2006, (large arena, overwelming really) as I approached the stage, my uncomfortable and too large pointy toe heel got caught in the floor board. I kicked them off and proceeded to accept my Doctoral degree barefoot. Fun times!

  89. I love Naturalizer shoes! I had a pair of brown pumps with fantastic orange details that were great to look at – but hellish to wear. No padding under the ball of the foot, too high of a heel… I knew they had to go when the deciding factor of whether or not to wear them was how much I needed to stand or walk that day! Life is too short for “sitting down only” shoes!

  90. In college I had a date with the quarterback of the football team! The QUARTERBACK! I was so nervous/excited and wanted to make a great impression so I wore my roommates Candies backless platform slides (think of the plastic Barbie doll shoes of our youth). They were extremely uncomfortable and awkward to walk in but vanity prevailed! We went to dinner and things were going well until on my return from the ladies room on the 2nd floor, my heel stuck in the last step of the stairs and I face planted on the floor in full view of the entire restaurant and my quarterback. Twisted ankle, leather upper ripped from the sole, skinned palms and pride shattered into a million pieces I limped to my seat. It definitely broke the ice and we did date for a year but I never wore backless mules again. Sturdy girl shoes please!

  91. Many years ago(70’s) when I was an impoverished medical student, also single parent with four kids, I was invited to a very posh dinner gala benefit etc. I had a dress that would work left over from the married days but no shoes. I went to Neiman Marcus and treated myself to a pair of gold Bruno Magli’s. I really couldn’t afford them but they spoke to my soul. I still have them, they are perched like an objet d’art on a dresser in a guest room. I think I wore them exactly once but they are still things of beauty.

  92. I have a few to choose from, that include blood/blisters/and emergency shopping but this one from my preteen years is probably the worst. Those plastic jelly shoes + 110 degree southern summer heat. I wore them out to walk to my friend’s house and they MELTED on the hot black asphalt and stuck to my feet. I had hot pink plastic melted all over my feet and my bare feet were walking on black asphalt and I was 15 minutes from anywhere. It took hours to scrape off the plastic and the hot pink dye had stained my skin. I don’t even want to think about the chemicals…the burnt plastic smelled horrific.

  93. I had saved up for a pair of shoes from a more expensive store than I was used to shopping at. I was so excited when I finally got them. I wore them the next day and after 1/2 a day of walking around campus, I had blisters in a few different places and started bleeding an hour later. I had to borrow slippers from a friend who lived on campus (different size feet and I could throw the slippers away).
    I couldn’t wear “cute” shoes for a while after that while the blisters healed.

  94. what a fun thread! Thanks, Lisa. I love those first boots.

    Forgetting the inexpensive and horrid high-school-dance heels of my past, the current winner for most uncomfortable pair are Prada — beautiful little kitten heeled, pointy toed slingbacks with an elegant bow. I tried them on and couldn’t believe how slender they made my feet look. Well, that’s because they’re a good 3/4-inch narrower than my actual foot. I do still wear them, but only on days when I’ll be doing a lot of sitting…

  95. On my first trip to England in my 20s, I thought I needed hiking boots for the trekking we’d be doing across fields, dales, and moors. I went to someplace cheap, like Walmart, but all they had was a half size too small and a half size too large. I went small, as the bigger ones made my feet look huge. (Oh, vanity!) I squeezed my feet into those boots and limped across the Lake District, Yorkshire, the Cotswolds, and parts of Scotland. Never again.

    These days, when we go to England, I pack a pair of Blundstones if we’re going to be going on any long walks with friends. Alternately, our friends who have a gorgeous farm near Bath have piles and piles of Wellies and I just borrow a pair from them.

  96. A lovely pair of tan sling-back kitten heels — shredded the back of my heels like nobody’s business, all the while giving me bonus toe blisters.

    I don’t know why I didn’t give them away after the first time I wore them; months later, I’d forgotten the pain and packed them for a business trip. I had nothing else to wear, and limped through a day. When I finally got home, they went directly into the giveaway bag.

  97. On my feet all day presenting a study to a client in Princeton. I had heels on that I thought were comfortable – but alas, were not. I was in such pain that the moment I walked out of the building, I took them off and walked barefoot across the parking lot to my car. I didn’t care who saw me at that point.

    My business partner and I drove to downtown Princeton and I bought a pair of flip-flops to wear on the plane. We then stopped and had a bite to eat at Panera, then drove to Newark Airport whereupon my business partner realized she’d left her handbag draped over the back of the chair at the Panera. Those Princetonians, though, were honest folk — we drove all the way back and it was still there just where she had left it. Barely made the flight on time – but very memorable on both counts!

  98. Back in the 80s some dreadful shoes called Jellies were popular. Basically they were transparent colored plastic shoes with cutouts. They were cheap and poorly made with sharp edges on the cutouts. It felt like knives were slicing into your feet in each of the little square holes. And yet us poor college girls kept wearing them!

  99. I’ve definitely worn some uncomfortable shoes before. The worst was an adorable pair of black mary janes with a kitten heel. After a few torturous wears, into the donate box they went.

  100. try this on for uncomfortable: shoes that literally disintegrated on my feet!…

    I’d found some lovely Aerosole low boots in soft suede and liked them SO much I bought in all three colors as my trusty standbys. After a couple of years I tire of them, styles change, so I put them in the back of my closet. Ten years go by, styles change back to low boots, and I’m thrilled to rediscover them one day and wear the black pair to a big festival at the Orange County Fairgrounds as there’s much walking to do and I remember them as so comfortable!… Half way through the evening I feel as it I’m stepping and tripping on stones, walking in a dry creek bed. My balance is all thrown off. I look at the bottom of my shoe and the sole is literally falling away in chunks, leaving an uneven rubbery grid and a trail of black crumbs behind me. One sole ends up completely gone, the other half gone, and I’ve got a shoe-induced limp at this point. LONG distances, and trust me – it would not have been a good idea to take them off.

    I contacted Aerosole later but they wouldn’t do anything about it. HA – good lesson on buying well made boots that last!


  101. I believe the guilty pair are still in my possession, moved to a sell-or-donate pile but still lurking here nonetheless. They are a lovely pair of mid-heel pumps in a tan and cream tweedy fabric with wood (faux?) stacked heel. Lovely, neutral, classic style and absolute agony from day one. The top of the back cuts into my achilles tendon and feels quite sharp. The toe box is too narrow (“they’ll stretch” is a mantra heard in shoe stores ’round the world!). Although they have lingered for well over a decade, they were only worn twice in the first year. I nearly wore them once more the following year but fortunately the pain kicked in before I left the house so I was able to change before damage was done.
    A pair of kitten-heeled black satin pumps with a pointed toe are a close second and I misguidedly wore them time and again, eventually learning to bring a pair of flats for the trip home.
    The selection above is quite enticing, and while the Salene and Lecture stand out to me, I’d likely select Jersey if given the option.
    My thanks and applause for the privilege of reading Privilege, it is a real treat. Brava!

  102. to quote George Takei, Oh Myyyyy! Doesn’t leather just do ‘it’ for you? A pair of knee high leather boots, a skirt or dress, some good fitting tights with top, scarf, and blazer. For me, that is being ‘put together’; it shows confidence as well as good taste too. I could conquer the world in an outfit like that!

  103. I have suffered through some very uncomfortable shoes. Probably the least comfortable (but worn often!) shoes were close to 5 inch heels that were leapord print with red patent heels & toe. The had the 1 inch front platform so they were so stiff & did not move with one’s foot. But they were so fun that I couldn’t resist even though my feet hurt for days after each wear. I just sold them on ebay. :)
    I love those jersey boots!
    Thanks for sharing!

  104. My poor feet….Ouch is the least I can say. I wore a beautiful pair of shoes to my son’s wedding, and forgot to bring another pair to slip into after the festivities. Needless to say, by the end of the night, I was in agony…My lovely husband was kind enough to give me a foot rub that night…Ahhh…..

  105. I can take a little pain in heels (although I rarely do), but what really drives me crazy is buying a pair of shoes because they feel comfortable and seem walkable, and then getting blisters. I used to walk to work and was always looking for cute, comfortable flats. I found what seemed like the perfect pair of black mary jane Campers. I tried repeatedly to break them in, but needless to say, every time I wore them I ended up with blisters. I think they’re still in the back of my closet because I tell myself I may wear them if I’m not doing much walking, but truth be told they’ll probably just sit there gathering dust. I really should get rid of them.

  106. I have bought shoes that hurt my feet for years. I save them in little boxes thinking I will wear them again someday because they are so cute or because I only wore them once (because they hurt my feet). I turn 50 in 2014 and with this new journey will be cute shoes that feel great. Love the blog.

  107. I had been hiking in Corsica, purposely wearing old tennis shoes intended to be trashed after the hike. While I hadn’t trained at all well for the hike, I had at least taken obsessively good care of my feet and had no blisters. Back in civilization, I had a couple of days to make my way back through Italy before my flight. I found an adorable pair of sandals (think dressed-up flip-flops with a slight kitten heel) and asked the store to just keep my sneakers to dispose of. Two hours later, everywhere the straps touched were masses of blisters, and I had to wear the shoes another two days. Sigh.

  108. A pair of 4 -inch heels bought from a discount shoe store. I wore them out dancing every weekend in college. No wonder I have back pain 15 years later!!

  109. There was a job fair at my undergraduate university the spring of my senior year. An organization I REALLY wanted to work for was going to be there. I went shopping with a friend beforehand and picked up a great skirt suit from Benetton, which I still wear, and black peep-toe heels. High heels. Really high heels.

    I am a sturdy gal. Heels are not my thing. But I wanted to look “professional,” and these seemed professional, and my friend was encouraging. So I bought them. I wore them over the cobble and brick paths to the student union where the career fair was held. And my feet really, really hurt. I took tiny, hobbling steps to meet with potential recruiters.

    I didn’t wear the shoes again. And I didn’t get the job with my dream company either. But that sent me down another path, one with more practical shoes and more realistic aspirations.

  110. For my first job at a major corporation, I bought a beautiful pair of navy kid pumps to match my “dress for success” navy suit. They were so uncomfortable that I had to take them off while working at my desk. One day one of the guys reached under the front of my desk, stole my shoes, and stuck them heel first into a planter. Imagine my embarrassment when I had to walk barefoot through the halls to retrieve my shoes!

  111. My junior year of college, I splurged on a pair of Birkenstock sandals. I then got one of my first-ever pedicures and didn’t know any better than to let the woman use the razor on my sole, exposing new skin ready to be chafed. Then, I went to Paris for 5 days to visit a friend studying abroad and walked around in my Birks.

    Result? Blisters on the bottoms (balls) of my feet. Ouch. It wasn’t really the shoes’ fault, per se, but I definitely associated the pain with the shoes. And I was so disappointed because they were supposed to be so comfortable and sturdy!

  112. When I was young and comfort shoes were mens wingtips with a heel and worn only by nuns, wooden soled clogs became the rage, so I wore them to exude the aura of Norwegian meadow-frolicking they marketed even though I lived in a city with concrete sidewalks. Then I took to wearing “sandals” that were actually heel-slapping slabs of wood made by a faux doctor and a perfect prelude to plantar fasciaitis. By the time I hit 40, the myelin sheaths in my feet swelled to squeeze the nerves in my toes like a vise, causing them to issue forth pain like a cattle prod. A needle full of cortisone allowed me to walk again and it was then I discovered the joy and real purpose of Birkenstocks which I had previously dismissed as the token footware of hippies and commune-dwellers. I now live pain free based on nothing but really good shoe choices, of which there are many stylish and comfortable options—finally. So glad I lived to see this day!

  113. The day is hot.
    The parking lot
    a mile from where I have to go.
    I’m late! My case is heard at one.
    I must trot there in the sun.
    My shoes – those heels with scarlet soles –
    Cramp toes, pinch skin. My tights have holes!
    I hobble, wincing, to the door –
    It’s locked – I have to trot some more!
    The hearing passes in a cloud
    of pain so bad I groan aloud
    each time I stand to face the judge.
    And still to car I have to trudge!
    When I got home that awful day,
    Those shoes were, pronto, thrown away.

  114. Oh, my saddest shoe experience was when I saved up for a pair of awesome Fluevog Minis (bombshell-o-rama, black leather with white trim and little bows) and then found that they were simply unwearable, putting pressure in the wrong places and leaving the right places unsupported, as most heels that aren’t designed for DanceSport seem to be.

  115. My most uncomfortable shoes were not towering platforms or needle-toed stilettos but innocuous little flats that had no arch support, rubbed across each toe and gave me heel blisters the size of silver dollars. But they were chic parrot green and navy blue and by god, I was going to wear them. I too will name Pappagallo. And they were expensive!

    PS I’ve bought Naturalizer shoes for years; they are a under-the-radar smart buy, long-lasting and very close in styling to shoes four times the price.

  116. My worst shoe experience happened recently when I wore these adorable kitten heels to my sons school. I just knew I was stylin’ in these babies. But, they were just a little too big, just the slightest. I fell down the stairs when my pretties decided to fly off my feet and you can imagine the rest. Oh my aching foot!

  117. I was traveling by land from Chile back to the US after I had completed my 2 years in the Peace Corps. By the time I got to Guatemala, my shoes were in pretty bad shape. The sole was torn off from the upper. I was in a tiny town outside of Tikal where the streets were nothing but mud and there were no shoe shops that I could see.

    So I bought some string and tied the sole to my foot so it would not come off as I trudged through the mud. With every step, I would sink into the mud and the mud would seep into my toes. I would lift my foot and the sole would only reluctantly release from the mud, giving a loud squish and slapping against the bottom of my foot every time it did.

    When I returned to my room, which was in a cinder-block structure and no windows, which is not a good design for a humid, hot climate, I had to wash my shoes and feet off at the tap outside the door.

    I kept those shoes tied to my feet until I got to that pyramid town in southern Mexico. Rats. I can’t remember the name. Anyhow, it was a city and I found some cheap cloth shoes there. The ones I tried were a little snug, but they didn’t have anything bigger and plus, the salesman assured me they would stretch, as shoe salesmen always do.

    They did not stretch. Not one little bit. I hobbled through Oaxaca, but by the time I got to Mexico City, my feet hurt so much that I was almost crying. I looked at shoes there, but I was almost out of money and returning to the US with no job and no plans. The nice shoes were expensive and I had already wasted money on cheap shoes.

    But I couldn’t take one more step in those cruel shoes. So I decided to buy some decent shoes. I would use my credit card and deal with the lack of income later.

    Only when I went to charge the shoes, the card was declined. I discovered that my card issuer had sent me a new card – to my mom’s house, which was the address I had on the card – and of course my mom had not activated the card. The old card was no longer valid.

    That’s when I said forget it. Bought the shoes with cash and went back to the US two weeks earlier than I had planned, because I had no more money.

  118. I bought some very pretty dress shoes with a sling back that slid down constantly making them difficult to dance in or even walk. I hung on to them because they went with everything and I hated to shop for new ones. I felt liberated when I finally let them go to a new home.

  119. My worse footwear challenge came when I attended a wedding. I thought I looked great in my dusty rose Armani skirt with matching silk blouse, neutral Wofford hosiery and my beautiful new black Cole Han pumps. In the middle of the wedding, my feet began to ache, really ache. By the time I got to the reception it was really bad. I left early and as soon as I exited the room, took my pumps off and walked in my stocking feel across a gravel parking lot on a cool November day to my car, drove without shoes home AND promptly sent the shoes to a consignment store. It was awful. I love the ease of the Naturalizers…love the black flats with the tortoise.

  120. Well this is a naughty story. My husband decided to spice up our bedroom sexy time and bought me a pair of um… Leopard hooker shoes. I swear the heel is so high I can’t walk in them. Which is I guess the point.

  121. I rarely/never wear uncomfortable shoes. I have never had tolerance for them, even in my youth (said with eye-rolling irony, as I’m 23). But shoes that look functional and cute can still be cause pain!

    I have a some classic ballet flats with a cap toe that have supportive insole and looked like the perfect combination of comfort and style.

    But they cut up the back of my heel, squeezed my chubby little toes to oblivion and eventually lead to mincing steps that quashed the Audrey Hepburn dreams I had for the shoes. But…I still have hope that I’ll break them in and they’ll become perfect. I still wear them occasionally, just with thick tights of trouser socks.

  122. Back in the 1970’s I decided that I should get Earth Shoes – they were supposed to be good for your feet because the heel actually tilted down. After a few attempts left me with really sore feet and ankles I decided that what was supposed to be good for you and what actually was were two different things. Since the shoes weren’t pretty I wasn’t even tempted to keep wearing them.

  123. When I worked at a coffee shop in high school, we had to wear all white shoes. The only pair of all white shoes I could find were Keds. Although they were cute, my feet (and back) were always a disaster after working longs days on my feet! In hindsight, I should have looked into some kind of insert, but at 16, that thought never occurred to me! I am much more informed now and really try to make sure my feet and back are happy in my shoes.


  124. Although I have been always loathe to look like a tourist and wear sneakers when sight-seeing, on a trip to Washington, DC, I knew I wanted to spend the day at The National Zoo so I bought a pair of god-awful ugly-bugly Mephisto sandals, not the thongs. Although they proved comfortable (though they looked like merde), I figured in a maxi sundress, no one would see them. By the time we arrived my Metro from nearby Tyson’s Corner, VA and got to the Zoo, it was hot and I was perspiring (Ick!), the beginnings of a blister was forming on the top of my foot where the “sandal” grabbed my foot. Thinking this must happen all the time, I checked into the First Aid station at The Zoo for a Band-Aid. But the perspiration made it impossible for the Band-Aid to stay on my foot and it escaped. Another First Aid station was in sight, I went to the Ladies’ room: washed and dried my foot, applied the Band-Aid to dry skin thinking that would surely do it. Nope. I put on 8 Band-Aids in 4 hrs. at the Zoo and by the time we left, I was carrying my expensive ugly shoes and walking barefoot, sure I would step in poop, on glass or a nail. I finally made my husband stop in a drug store where I bought a box of band-aids and a pr. of tube socks. (They didn’t have any moleskin which would have solved the problem). I put on the socks and wore those as “shoes” until we reached the Metro. I put back on the black Mephisto sandals which now looked totally ridiculous with tube socks underneath until I realized that I looked very much like an Asian tourist minus the camera. I also stood in great pain during our 1 hr. Russian Orthodox wedding which includes walking around a small altar 3 times. After the service, I took off the lace sandal to find a nail had gone through the sole of the shoe at the ball of the foot. It wasn’t the shoe itself. Luckily, I had brought another pair a peau de soie low heeled pumps to wear to the reception and could change ASAP.

  125. I once had a pair of black nubuck slingback Marc by Marc Jacobs heels (four inches tall, too) that were a half a size too small, because I had found them at a consignment store and loved them so much (they had a round toe with menswear-style brogue detailing) that I talked myself into believing that they fit. I wore them to my cousin’s wedding a few weeks later. Thank heavens they had the sense to have an open bar or I think the excruciating pain in my toes would have kept me from having any fun at all. It’s a rare pair of shoes that can drive one to drink.

  126. I flew home suddenly to attend a funeral, and forgot my favorite black shoes. A rushed trip to the only shoe store on the way to the funeral resulted in the worst shoe purchase of my life! As I stood in the drizzle graveside crying, my feet felt as badly as I did on the inside. Miserable day.

  127. Manolo Blahnik made the most beautifully spectacular peep-toe almost-stiletto pumps in patent leather about 10 years ago. Beautiful for standing on cushy carpet, but definitely not for the hob noble gobble (a fundraiser for detroit’s thanksgiving parade) on a click-in-place floor (50 cement steps down from street level) on the field at Ford Field ( home of the Detroit lions)- complete with carnival rides from the end zone to the 40 yard line, and dance floor from the 50 to the 25, and an uber-excited 7 year old to chase after. It took at least 3weeks before I could feel my toes…

  128. My aunt had a collection of great Papagallo shoes, the ones with the flower on them. She also had some other skimmers that were so cute, and she told me to take whichever ones I wanted, since she wasn’t wearing them anymore. One pair was straw with a great grosgrain trim. I wore them once and by the end of the day, the straw had stretched sooo far they were flopping on my feet. Chucked them right out.

  129. I have some grey 4.5″ stilleto-heeled ankle/shoe-boots with ruching around the ankle, which dips down at the front of the foot to show a bit of ankle cleavage. They sound awful but they are the sexiest footwear you’ve ever seen. They make your legs look a thousand miles long (even if, like me, you have endearingly been nicknamed “Stumpy” by your younger sister), they add a touch of sass and rock-and-roll to a classic black dress, or snuggle in next to your favourite jeans. They are French.

    I wore them out dancing in Soho one night. It was close to Christmas, and I wanted some warm and rain-proof footwear to wear there and back – and equally didn’t want to put said clumpy footwear in the cloakroom at the hideously pretentious bar we’d been invited to by one of D’s work colleagues, so I wore these boots, with my favourite black dress, black leggings (flashing that bit of ankle cleavage), fuchsia lipstick and my favourite silver glitter clutch. The outfit was perfect: less obviously pretty and a little bit cooler than the party dresses most of the other guests had poured themselves into. It’s not often I get an outfit quite so right, and it felt amazing. I drank whisky cocktails and danced into the small hours, not sitting down for a second until we were on the night bus home.

    At which point I noticed the balls of each foot had hidden themselves beneath blisters piled on blisters. Standing up to get off the bus was searing agony. I stood at the bus stop in the pouring rain, looking up the hill, and knew I could. not. walk. another. step in those bedevilled boots. So I took them off and hobbled home on my bare blistered feet, along the gritty wet dirty London pavements, up the hill and down the other side, feeling as if my feet were on fire. It took me thirty-five minutes to make a journey which I usually walk in ten.

    I have never worn those boots again. I am still planning to. :-)

  130. (In case you are wondering why we didn’t get a taxi, there were none, and why my beloved didn’t give me a piggyback, he’d just hurt his knee running and was hobbling too! The knee is an ongoing problem a year later. Most annoying!)

  131. Oddly enough, a pair of Saucony running shoes. I’ve had surgery on one (high) arch and when I could walk again, I thought I’d try what runner friends insisted was an excellent running shoe. I always wore Nikes, but my friends insisted they were for show, not function.

    So I tried the Sauconys on a run and soon discovered that my operated-upon arch was and is extremely sensitive to any kind of arch support in a shoe. The left Saucony tormented my arch (via an irritating pressure that became painful–difficult to describe) to such a degree that I took it off and walked home barefoot. And I’ve worn my “stylish” Nikes ever since.

  132. Being in the Navy, you could argue my most uncomfortable shoes were the Army combat boots I had to wear to pass the Battle Fitness test…uncomfortable physically and spiritually.

    My most memorable shoes were the strappy sandals I wore to my senior prom. I had broken my foot only days before and my pretty, frothy shoes that matched my pretty frothy dress were a no go. I bought some horrid, ugly, strappy Birkenstock style sandals, opened to their widest hole to fit over my cast and….DANCED THE NIGHT AWAY. Ugly, painful, but so awesome.

    The stories on here are amazing. Thank you everyone for all your sharing…I sit here chuckling in my living room, and loving every minute of you all!

  133. I can’t guarantee that this is the most uncomfortable EVER, but definitely within memory…. I did what I should not do, having a very slender heel compared to the rest of my foot, and BOUGHT SHOES ONLINE, without trying them on.

    So, orange Boden shoes that were so cute and on sale, you rubbed my feet raw within two hours, and then the decoration on the toe of the right shoe fell off! Bad Boden shoes!

  134. I’ve suffered through many awful shoes, but I think the worst were a pair of silver, strappy heels I bought, and didn’t break in, for a Vegas trip. They cut/blistered every part of my foot they touched, but I was too afraid to take them off and walk barefoot on the Strip! I spent the rest of the trip miserable and covered in band-aids…never again will I do that!

  135. Oh, it is hands down my first pair of blush satin, beribboned, foot destroying Capezio pointe shoes. I was 10, I had longed to be “up on pointe” like the beautiful ballerinas I had admired so long, and I was so thrilled when my teacher finally pronounced me ready. My mother drove through a monsoon to buy me those shoes, she sewed the ribbons on herself. I don’t think either of us would have been so pleased or proud if we had known what those shoes would do to my feet, how hours of practice in them would twist and mutilate toes, knees, hips, back. That first pair was stained with blood.

    I would never have traded them for the most comfortable slippers in the world. I still have them, in a box filled with relics of my happiest memories. Women suffer for beauty, they suffer to make art.

  136. My tale of foot woe begins with trying to recapture my youth. In the days before kids, I did commercials and industrial films. And after years of being at home, I decided to dip a toe back into that water and sign up with an agency that provides “background” (extras) on commercials and movies. I was excited to be chosen for an airline commercial where we would be “elegant party-goers celebrating the new plane.” I brought along my most comfortable black alligator pumps. I wasn’t worried- they have that air-cushiony thing…just a few inches high… no problem right? What I didn’t realize was that we would be on our feet for the whole night, pretend partying, standing in front of an airplane at an airfield… with camera rolling, multiple takes, over and over. We went into overtime. My feet began to scream. Not only did the air-cushion feel like concrete after a few hours, but the heels seemed to be driving directly into my hips. Between takes, I would slip them off, but this crew was so efficient we barely had time to sit down before being called back out on the tarmac. I hobbled home at 2:00am, and could barely move the next day. So if you see a commercial for Cathay Airlines with someone in the background in black pumps moving like Frankenstein- that’s me.

  137. I once bought (what I thought at the time) the most beautiful leather black pumps for an interview in NYC. I was young, but smart enough to know the importance of good footwear. I walked the 26 blocks from Grand Central and felt searing pain. The nails had come through the heel of the right foot leaving me with stigmata. Oh the pain and blood. So gross. No time to change shoes. When asked in the interview if I dealt with “uncomfortable situations” well, I think I burst into hysterical laughter. Ouch!

  138. I wanna play!! We were going on a trip to Europe with a two day stop in NYC. I’d bought (what I thought would be) a super comfy pair of flats, gum soles and everything. Our first venture out in NYC was a brisk walk from the Parker Meridian to The Palm restaurant for lunch. I didn’t even make it to the Palm! The blisters I’d rubbed were raw and painful. I had to stop at CVS and buy $$ worth of bandaids, blister protectors, bunion rings, etc. What a mistake. My feet were a mess for most of the next two weeks that we cruised the Mediterranean. LESSON: Even the most COMFY shoes should be WELL broken in before a trip!! Thanks for listening!

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