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Retirement Dressing: Do Not Go Gentle Into That Good Night


One of you asked, what happened to the retirement dressing project?

Good question. Let’s take a look.

After a brief detour through $200 sweatpants (I did find a good pair at La Garçonne), I reverted to something I learned in software. The Use Case Methodology. Dressing to fit my real needs. But those are minimal. I’m 57. I’m newly married. I get in and out of the car a lot, and walk on sidewalks. I have no particular point to make to anyone about anything. In this context, what matters?

As users will, I have requirements.

  1. Comfortable Feet. I’ve always insisted on comfort, but for now my tendonitis requires extreme measures. Including the only pair of Nike Air Max I could find at the Stanford Shopping Center, in sky blue camo print. Yikes.
  2. No Tight Pants. I started work in 2011 wearing baggy pants. I sucked it up, literally and figuratively, because ill-fitting pants do not convey competence. But I’m retired. You’re just going to have to trust I’ve got things under control. Despite that loose waistline.
  3. Layers. Northern California weather is rarely cold, but often cool. Layers, as we tell all the poor shivering tourists, are critical.
  4. Sense Of Self. Once we solve our base physical needs, we wonder, “Hey, who am , anyway?” My list:
    1. Female
    2. Intellectual
    3. Unfussy (AKA Sturdy)
    4. Left Of Center, But Not Too Far (Yes, personal style is political, whether intentional or no)
    5. Slightly Raffish (Definition #2, please, and there’s the tricky part)
    6. Drawn To Beauty

That’s Not My Age has suggested that my style be called Elegant Tomboy. As I’m not sure that anyone wearing sky blue camo Nike Air Max sneakers can be called elegant, I’d tweak the term. Refined, perhaps? Except that makes me think of teacups and pinky fingers. Soigneè? Or maybe just Suburban Tomboy, if we throw all aspiration to the wind.


Maybe Goofy Tomboy is most apt.



And the garb?  Turns out I’m a button up your pants and get going kind of gal. I like to feel like I could pull my weight, even if I don’t have to. The emergent retirement uniform includes:

  • Jeans – GAP 1969 selvedge (these are Original Fit, not available right now)
  • Knit top – usually a t-shirt (button fronts constrain my shoulders, fine for work, but to be avoided when possible)
  • A tough jacket – is there anything better than a biker jacket for the soignée tomboy? I think not. (Now in brown at All Saints)
  • Flat, laced shoes – As my foot heals, I will return to the oxfords of yore.


However, if I stuck to the above list, I’d be ignoring my #1 sense of self. Female. As humans age, the genders converge. I want nonetheless to participate in our cultural constructs around femininity. In a Sturdy way, of course. Since I’ve never been one for girlishness or vamp, ruffles or statement pieces, I have my own way of signalling.

  • 100% flattering colors, mixed with a little sophistication. In this very casual mode, I have no style points to spare for questionable colors, no desire to balance out yellowish clothing with blue-ish lipstick. Looks like I’m gonna be wearing a lot of blue.
  • To maintain the right masculine-feminine balance for me I add some movement, something graceful. The turquoise earrings dangle just enough. One could still hang upside down on monkey bars. Scarf, which you’ve seen before, is by Etro.

Finally, I’ve decided to let my gray hair grow even longer. Absent work, I really can’t be bothered with blow-drying, so shoulder-length is out. If I’m going to dress this (to put it bluntly, butch, adding a cropped do would misrepresent. So long, and in a braid, it is. Even a hair ribbon. I’ll have a hair person put it up for anything fancy, and wash and let fly for date nights.

This project is by no means over. I want some more dignified sneakers, along with some looser, boyfriend jeans. Still working on raffish. But it’s a start. I could show you something more impressive, but style isn’t stylish if you never wear it out of the house.

Images are mine. Suburbs are everywoman’s. I thought I’d try my hand at a Pinterest manifesto for us midlifers. And some affiliate links used here may generation commission to be donated to Dress For Success.

69 Responses

  1. I still think Elegant Tomboy is the best description (definitely not suburban) and I like a comfy shoe/the Air Max. You should keep an eye out for the Nike x Liberty collaborations.

  2. Looks like you have made/are making the transition beautifully.
    I’m a 58 year old stay at home mom of two teenage girls (15 and 18-you do the math-late to the party!) and this is basically my uniform also.
    Not sloppy, don’t want to embarrass the kids.
    But comfy and practical and the scarf always adds that extra touch.
    Great jackets and scarves over jeans in the winter. Light cardigans over tanks in the summer.
    Flat riding boots, low heel shorty boots, Toms, and Uggs. (I’m in Colorado-Uggs are allowed.)
    And always always dangly earrings and beads. Always. Pearls are perfect to elevate jeans.
    Good job. You look great.

  3. I think the term Elegant Tomboy fits quite well. I like to think that’s what someone would say about my style too as it’s very similar. I’m not really retired, but as an artist and grandmother who does babysit 3 x a week, and then rushes to my studio, it suits me and my lifestyle well. And if we’re going out to dinner with friends, I generally only switch up my shoes to booties. I love New Balance sneakers in gray suede. So comfortable and good with blues!

  4. You look great – polished and relaxed, not easy to pull off. Nothing butch about it at all. This is the kind of feeling I’ld like to project, not there yet but trying.

  5. Oh, I really like Sue’s suggestion of Polished Tomboy — the perfect adjective, imho. I’d never noticed before how close yours and Alyson’s styles are, at least in this particular iteration. What she’s wearing in her latest post (on scarves) I could easily imagine you in, and vice versa, no?

  6. Love your blog. Read it religiously.
    1. I agree about statement pieces or “heros”; they make me antsy.
    2. I would have thought beauty would have been higher on your list, closer to intellectual.
    3. You don’t seem to be a purse person.
    4. Have you tried Super Feet Insoles. I’ve had excellent results with them.
    5. May I suggest “Smart Cookie”. :)

    1. @Theresa, #2. You are right. I’m in denial, I think and this post is proving to be an eye opener. Who needs therapy? I wonder why I dismiss beauty, or at least discount it. Hmm. And I have a purse. I put things in it:).

  7. Being possessed of the feet from the 7th circle of hell, I am no stranger to having problems buying shoes. has saved me. Free shipping, free returns. I can bracket sizes if I’m not sure how a shoe will fit, and returns are easy. Print a shipping label, drop the box off at UPS. Superfeet are good, too. My current pair of shoes are bright blue, I’m not loving that color, but they don’t hurt.

  8. Off to source super feet, my feet have been awful since birth when they had to be wrapped for months on end – obviously a selkie/mermaid.

  9. Your jacket has fabulous detail and it’s a great fit on you. I like this unfussy approach as it seems like an honest representation of your lifestyle. It is important to have decent walking shoes.
    I have some serious walking shoes too…I wear them when my walking partner and I do our weekly 10K walks.

    1. VERY cool, I’m smitten! Do you wear a sock of any sort, if so what thickness – and how did you find the sizing [with or without sock]: true, short, long? Some of the reviews complained of slipping on wet surfaces, what has been your experience?

      LPC, I’ve run out of superlatives for you my dear, you are just TOO DA*N COOL. As is your brother, what would you do without that scarf [rhetorical]?

  10. I often think of myself as a”tomboy” dresser. Comfort is everything in my work as an antique picker. I have a recommendation for a great running shoe.The vintage nike running shoe available at J Crew. Comfort, classic and dare I say, “chic?” I wish I could find them in every color of the rainbow, to match my earrings. Because, yes that girly side of me need to have a fabulous earring dangling while my jeans and foot ware must say classic comfort.

  11. You look fabulous and you’re right “goofy” in those shoes. But let me tell you I understand the need for good shoes. I have to wear “MBT” shoes for Planta Faciitus so I understand completely. You know woman, you have style up the gazoo, so it’s always a treat to see what you’re up to and what reinvetion you’re into. Just enjoy the ride in what ever suits you for the day, week or month.

    You’re just plain basically beautiful.

  12. I like the fashion description very much indeed! But are you consistent with it? Just wondering bc some people sway. But love the fit of your jeans as they are slim but loose all at once but then again you look slim so…

  13. Personally, one of the most exciting things about becoming ‘a certain age’ is that we have the potential to choose and develop a style that reflects our true selves, rather than it being dictated to us by forces that may have previously had more influence than we’d like to admit. Instead of lamenting the loss of youth, we can go forward to finding what really suits us, what we enjoy, and the need to make a particular point (hopefully becomes) a choice. I’m loving my super short haircut, even if the Hubster isn’t so sure. After 28 years of marriage, I don’t’ think he’s hanging around just because I have long hair (or not). Vive la choix – we are free!

  14. All you need is a knife in hand and you are ready to be a floral designer.

    And gays have long hair too, so be prepared for the admiring glance sent your way as you saunter down the street looking all hot.

    Just saying..

    xo J

    1. @flwjane, I only wish I had enough strength and talent to be a florist. And I am really embarrassed that I said something which required the reminder that gay women have long hair too:(. My sincere apologies. I accept any admiring glance happily, but have been chided in my past for clarity of signals and am now over-sensitive. You are a good sport, and I think you.

  15. This post resonated on so many levels, especially after a week of realizing that any heels over 2 inches have to be retired. An exit is always an entrance of course, and I’m discovering the delights of mary janes with sensible block heels.

  16. I think you look great, and the braid adds a little artsy to the ensemble – I may just think that because my favorite childhood art teacher had a long braid. I am now thinking about how to concoct a similar vibe in my MUCH colder location.

  17. Whatever you call your look, it’s fabulous. Scarves and the right earrings can elevate any casual look. And a tough girl jacket should be in every woman’s wardrobe, leather or denim. Biker preferred if in leather. By the time we’ve reached our fifties, we’ve learned that comfort is key and never has to look frumpy. The coolest women I notice on the street are usually “of a certain age”.

  18. I bought a brand new and beautiful Etro scarf at a consignment store last week. It is black and ecru and lovely. It was a find!

    I’m 61 and a retired homemaker(!) But, I live in Dallas and living in this city requires a bit of a dress up for my daily rounds. That’s one reason I love being at our farm where no outfit could be called too casual. Even so, I like to look nice and pulled together.

    You are looking great! I’m going the opposite direction with my hair–I’ve cut it up to shoulder length. I don’t mind blowing it dry

  19. Cecil Beaton said that as women age, they should dress like either a young boy or a little girl, which makes a wacky kind of sense. I’m still going for ” matron at World’s most expensive prison.”

  20. Lisa… This is such a fun post… I love your self descriptions…

    The most important thing for me… reading between the lines… is that you have great self confidence and you really know who you are…

    That to me, is the hardest part of all..

    Very cool… in a word… :)

    Happy holidays and have a wonderful New Year… xv

  21. I was thinking Grown-up Tomboy, but that would imply being a grown up a lot more often :)

    Polished Tomboy is definitely a possibility. Maybe even Soigneé Tomboy?

  22. Yes!! Your hair is absolutely perfect, and I applaud the longer length in grayish. You look classic, you could be dropped down anywhere and look good. The clothes are right too, your inner comfort and confidence go past any fashion statement feebly made. I think, yes, the confidence. I am striving for that as I go up the age ladder. I look at photos from all over the world of older women, the old Navajo mommas, the chinese granmas, the sicilian nonas, and the longer braid is there. No silly hairdos with lowlights. The beauty in the face and the look behind the eye are the beauty there. Good work. Love the colors too. Oh, ps…..see lots of braids on the young budding beauties too………Think about it.

  23. ‘Personal style is political, whether intentional or no’ … thank goodness for recognition of this! My personal style is preptastic, my politics, not so much. I am by nature a high sturdy meets grande dame, and dress to match, but my political and intellectual leanings are artsy-sturdy to say the least. It’s a balance I haven’t managed to achieve, so find people making assumptions about me all over the place.

    Incidentally, I think those shoes make your outfit. Entirely wonderful.

  24. You look great, regardless of what you decide to call this style. I second the suggestion of Zappos for shoes. Lots of styles and choices, free shipping, free returns. At the suggestion of my podiatrist, Brooks Ariel is the style I wear, day in and day out (high, long arch, wide forefoot, really narrow heel, prone to both Achilles tendinitis and plantar fasciitis). It’s so supportive that on a good foot day, I can forego my custom orthotics. I actually love the Nikes you’re wearing. Whatever you decide to do with your hair, long, short or in between, it’s really no one’s business but your own. I’m struggling to understand. You say someone “chided” you in your past for “clarity of signals,” whatever that means, but there’s no set dress code or hair style that signals sexual orientation, as I am sure you are aware.

    1. You are quite right. And it’s something in my personal history, that I didn’t have front and center in my consciousness as I wrote, but clearly was affecting my thinking.

  25. I think you’re raffish already! This is my favourite look among women (relatively) my age: not sexless, not butchy, but with some grit.

    ^^ what you wrote, and also clothing quality is very important in retirement years. To still wear good clothes (not super-luxe, but good) is important to me; somehow I look more graceful in them.

  26. How about Feminine Tomboy? Or Tomboy Femme? That’s what me and a lot of my friends call ourselves. We’re coming from a queer perspective, though.

  27. I’ve been wearing a braid lately too, and so it doesn’t code Carrie-in-Sound-of-Music, I leave a good 3.5 or so inches of unbraided hair to fall below the elastic and swing it to the side (my hair goes fairly far down my back, which never fails to surprise when I catch myself in the mirror. It hasn’t been this long since my first year of graduate school, during my tender 20s).

  28. Style after mine own heart. I have never felt more at home than in a soft shirt, jeans, and tomboyish jacket. Glad to find someone else is, too. (: I have a very similar jacket, actually. I should wear it on my blog, too.

  29. I find I’m getting impatient with all those definitions especially since they still mean different things to different people.

    Actually I’m with theresa: you clearly are an aesthete, and there is playfulness and humour and inquisitiveness which in itself transcends narrow definition. And that middling to low contrast thing suits you wonderfully.

    1. I didn’t use to like the definitions either, until someone else gave me one I kind of like. An aesthete. How lovely. xoxox

  30. love everything – especially the nikes…and i second trying to find the liberty print version. they would suit you nicely. also try the gap sexy boyfriend jeans – i like mine very much, although after over-indulging lately and moving (getting out of my exercise routine), they fit more like skinny jeans than slouchy boyfriends ;) they’re good though – 100% cotton, which i like.

  31. For starters I love your hair! I think because we are over 50 doesn’t mean we can not have long hair as we did when we were younger. I think it being that long seems to fit the style you are going for.
    A will agree with others who have called your look a Polished Tomboy.
    Retirement dressing.. nothing wrong with jeans, and the jacket? In Northern CA we need something to keep us warm but still look stylish.

  32. For those of us with finicky feet, check out BarkingDogShoes.ccom. It’s great to identify possibilities for your particular needs, then order online….it saves trekking to lots of shoe stores. Long treks and sore feet are a bad combination for shoe shopping! Good luck and happy holidays!

  33. Lisa, I just love this post! You look wonderful and I look forward to reading more about this project. I would love to know if you’d consider jersey dresses either wrap styles such as by DvF or simple tees or shirt shapes. Wishing you a fantastic New Year celebration!

  34. I love your leather jacket! I am considering purchasing an All Saints biker jacket, but at 46, a little fearful as to how to pull it off. I like the scarf and jewelery you paired it with – it looks so biker chic! Thanks for the inspiration!

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