Privilege Blog

Building A Thoughtful And Stylish Retirement Wardrobe: Part I

I’ve been asked, what about building a retirement wardrobe — while you are still working? Good question. Few people write about the topic; misconceptions abound. Am I the only one who imagines racks of lavender terry jogging suits and puffy white sneakers?

I suspect many here hope to enter their later years in style, but also to set aside uncomfortable shoes, too closely-tailored garments, and hair chicanery. We may not be fond of the overly-cossetted look.

I need two posts to fully answer, today is State of The Union. On Thursday (or Friday) I’ll give an account of what I kept from my on-the-job purchases, what I got rid of, what I’ve bought, and what I’m still looking for.

As always, we ask which Use Cases are we addressing? And, what is our Release Charter? Release Charter here meaning Top Priority. Only one thing at a time can be the Most Important.

What Is Your “Release Charter?”

For me, comfort is paramount now; self-presentation a subordinate but persistent goal.

What Then Does The Use Case Methodology Tell Us?

I write, I clean house, I garden. I cook, I work out, I do errands. I occasionally go out with my husband, or with my family. You may live otherwise; engage in more formal socializing, take a volunteer position, run, bike, or practice Bikram yoga.

For now, when I’m home inside I wear flannel PJ bottoms and tanks and sweatshirts. We’ll put that stake in the ground. Housework is remarkably kind about my jammies. In retirement you dress for yourself and your own life.

Now let’s jump directly to the clothes I wear outside the house, taken from my actual drawers and closets. All High WASP ancestors, raise an eyebrow.

What My Closets And Drawers Look Like Today – By Clothing Category


From cashmere MaxMara, through an assortment of menswear-inspired light jackets, past a 10-year old $25 parka from Shanghai, to an old fleece in case I ever ski again. Californians need layers, outerwear can define our style.


Californians also, as I have said, need jeans. We can survive an entire year without putting on a single pair of wool pants. However, I’m in the process of deciding whether I have aged out of shorts except when temps top 85℉. Perhaps.


I find it easiest to put what I wear daily in one place. Hence, drawer tops vs. hanger tops. I have more drawer tops than you see above, several sweatshirts and a few cashmere v-necks but trust me, they are all gray, purple, or shades of blue. I wear the leopard tee, which is from Paris and 20 years old, once a year when the mood seizes me. Last year, with Doc Martens.


Will I ever don a pencil skirt again? The gold sequin one, sure, of course. The J. Crew stalwarts, perhaps no. I am not ready to say. The amorphous dark fabrics to the left are a pair of J. Crew black silk trousers and old Armani navy linen wide legs. In case of Texas.


The metaphoric forest to the far right is Issey Miyake. 20 years old. I wear it once every 2 years, because it’s scratchy. Works of art are allowed to scratch.


For social outings of one sort or another.


Need I say more? Am definitely aged out of those seersucker Sperry wedges with ankle ties. How quickly things change.


Fancy. Dresses and a skirt for warm weather resorts, my Italian suit just in case, a Mexican maxi from some time in the 1970s. I begrudge no piece its space; this is where I stash my vibrant color and large-figured patterns.

The True Categories

The thing is, clothes are not software. And so, on top of the use cases, we layer categories of the heart. Here are mine.

  • Sentimental Keepers: A cheongsam I bought for my daughter’s prom, even though it arrived stained, and unwearable; Carolyn Charles two-piece gown; my wedding dresses; a long brown columnar silk velvet shift I wore for Christmas when my children were young; a Bruce Springsteen t-shirt; others.
  • Special Occasion To Make Me Feel Gorgeous Even Now: Dresses by Tory Burch, Narciso Rodriguez, Christopher Kane, Prada, Dries van Noten; pleated top by Issey Miyake; tweed and velvet jackets by Chanel and Jaeger; shiny shoes by Rene Caovilla, Jimmy Choo and J. Crew; black silk pants; family jewelry.
  • Errand Clothes: Faded jeans and khakis; so many tees; cotton or down jackets; raincoat; wool and cotton scarves; big earrings & small necklaces; JORD wood watch; flat shoe brands that young women wear.
  • Nifty Items To Dress Up Errand Clothes For Social Engagements: Wool, velvet and tweed jackets; dark wash jeans;  tops of the constructed or embellished variety; Valentino Tango pumps and Dickers ankle boots; more jewelry
  • At Home Inside: Flannel, tanks and sweatshirts
  • At Home Gardening: Random clothes, all too large, all good for protection from sun and prickers
  • Workout & Swim: As one does
  • Currently On Probation: Pencil skirts, slightly-constricting button-front shirts, my beloved Commes des Garçons fierce heart tee, as it shrank and now shows my stomach, motorcycle boots and Sperry wedges, a pink cardigan. I love it in my closet but never manage to put it on my body.

I am curious, do you all keep clothes you know you will never wear again, for sentiment? It’s not a habit I plan to change – low downside. But I do not know if others do likewise.


Other posts I’ve written on retirement dressing, here and here. Also recently retired, and writing about their clothes from time to time, are Materfamilias and Hostess of the Humble Bungalow.


62 Responses

  1. I hold on to a few sentimental items, but not much. This post is inspiring me to do another closet clean out. I have the Valentino Tangos in cognac and black – best shoes ever for sprucing up a bit – great with jeans and dresses, and so comfortable.

    My love of cotton flannel is beyond words…..

  2. I retired two years ago and my daily uniform sounds much like yours. I have spent the past 2 years clearing out my closet and what I do not sell on ebay I donate but I do have a stash of shoes (mostly boots and dress shoes) and clothes that I know I will probably not wear but I will keep for sentimental reasons or because I just love them!

  3. I don’t keep anything I don’t hope to wear again. Wedding dresses get a pass – I have my mother’s even though it would never work for me if I did marry.

  4. Nope! Living full time in an RV forces one to be ruthless. If it doesn’t fit, or isn’t comfortable it goes out. If if hasn’t been touched in year, over the side. The only exceptions are jackets, just in case we end up (by mistake) where it’s cold.

  5. Rushing off to Bear a Mace and lead a bunch of newly convoked grads to the stage and off into their lives, my last big pre-retirement gig, one I’ll be wearing dramatic robes for. Really appreciate the openness of your wardrobe-sharing and I find your organized approach useful to thinking through where I’ll be going with this. Thanks for the hat-tip!

  6. I have my father’s army fatigue pants, that I used to actually wear (ah, high school!). Also, my wedding dress, why, I don’t know. I have no daughters and the last girl my stepson brought home could have made her dress and probably the entire wedding party’s dresses out of it. The rest I wear. Installing new closets was the best cleaner outer ever.

    1. @Patsy, Patsy, My daughter in law chose to wear my wedding dress! I was beyond surprised—you just never know.

  7. This is one of my favorite posts of yours ever. Do I keep sentimental items? Yes, but I don’t think I should. What do I have? I actually have some of my childhood dresses–made by my mother. Some are smocked, others have lots of braid or trim. If I have a photograph of myself in the dress, it is hard to let go. I also have the ensemble I wore to our older son’s wedding thirteen years ago. Is it lovely? Yes. Will I ever wear it again? No. It should go.

    No flannel PJ bottoms here (I wear only cotton knit nightgowns), but I do have my workout pants/tops which I wear whether I am working out or not.

    I always dress nicely to go out of the house–no matter where I am going. You will never catch me embarrassed by how I look. At the same time, I find it hard to invest in outfits that will be seldom worn. My shortcoming is too much practicality. I “make do” too often.

    1. @Susan, So glad you liked it! Let me affirm two things, even though you haven’t asked me to:). 1. You can keep sentimental clothing, as long as it doesn’t crowd out other pieces you actually need. 2. Invest in the special. No need to “make do.” You are investing in your memories, your sense of self, your identity. xox.

      1. Just pretend it’s a range, cabinets, or a sofa! You’re building life processes and aesthetics around it. And, SO earned.

    2. @Susan, Point well taken. You know that i have NO difficulty buying high end appliances, antique furniture, custom rugs, etc. My houses are worthy–so I should be as well!

  8. Lavender jogging suits and white tennis shoes!! I love that. Here’s another: high waisted, light colored jeans with a sweatshirt that has a white collar and is embellished with a kitty-in-a-teapot picture. White tennies present and accounted for. Don’t forget the short,grey,perm.

    My retirement wardrobe is pretty similar to yours, heavy on the khakis. I have given up shorts, no one needs to be treated to the vision of varicose veins and age spots.

    1. @Mary Anne, I am all for high-waisted jeans, but I have to say I doubt a kitty in a teapot can be found in the San Francisco Bay Area. ;)

  9. I am looking forward to another installment on this as I’m very curious what is on your “still looking for” list.

  10. Love your approach to the retirement wardrobe, your methodology is most thoughtful. I’m changing my thinking about my clothes as I get nearer to retiring so I’m reading with interest.

    Funny, although I mostly wear grey or black in the photos I was really drawn to your fancy items. I have a few things I keep just because I like the colour and pattern, but I hardly wear them. But as you say, if there’s space in the closet and they don’t interfere with the useful, why not? Who knows perhaps I’ll go crazy with colour when I’m out of the office for good.

  11. Yes, I certainly keep clothes I think I shall never wear again, but of course, hope to. The frustrating thing about living in the Bay Area is one requires a lot more layering, hence more items to store/stash away – ugh! At least in England we had summer clothes and winter clothes and with the use of an umbrella, year round, one could get away with a relatively compact wardrobe.

  12. Well we all know florists don’t retire, they just fade away….

    I’m with you on the shorts, but when it’s over 90 degrees all restraint comes out the window.

    I wear as little as possible. I sleep in flannel or cotton, often find myself gardening in them the next morning.

    I live in jeans and work out clothes wear the same discreet jewelry every day and now have a large assortment of hats for skin protection.

    Sounds like I could retire….

    xo J

  13. I have two sets of clothing – my every day (retired and living in a rural area) jeans and t-shirt stuff, and my dress-up and prance around in front of the mirror when no one is home stuff (this is actually my favourite). I’m newly retired, well, semi-retired, and have the time to investigate fashion a bit – so I take great pleasure in “finding” something unusual in the consignment shops, both bricks and mortar and online – way more satisfying (to me) than most of the offerings at the mall. The looking part is the most fun – fits in with my prance around mode. Then every once in a while I take something from my dress-up set and combine it with my every day set – and voila, I’m a fashionista! At least I think I am, and isn’t that what its really all about?

    1. @Elizabeth, I love that. A “prance around mode.” And yes, fashionista is often just one unexpected piece that lights up everything else.

  14. These are my use cases:

    -around the house: jeans and Ts and fleeces in cool weather, jorts and Ts in warm weather (I understand jorts is pejorative and I don’t care)

    -3 volunteer gigs
    a) Habitat for Humanity construction, which gets its own drawer
    b) ESL tutoring (casual)
    c) singing at bedsides (casual, modest, no black tops)
    Categories b and c played very nicely with my software industry wardrobe, but now that it has been a few years since I left, I’ve softened the look a bit with some Artsy Cousin items.

    -Dates, book club, etc., for which I display a bit more flair

    -Occasional wedding, fundraising gala, etc. I have gotten rid of a lot of things but have kept a few dresses and low heels.

    -Lap swimming, serious hiking (as opposed to running out locally in whatever I’ve got on), etc.

    Of course layers because I live on the San Francisco peninsula.

    I do have a few sentimental clothing items, but most of the sentiment is contained in family costume jewelry, which I wear for the “dates, book club, etc.” category or dress-up.

  15. Thank you for the mention Lisa.
    I do tend to purge my clothes often…my wardrobe has shrunk in size since retiring. I enjoy getting dressed so much more now that I can see everything easily.
    My style has evolved since I started reading blogs and I feel that I am dressing much more authentically….not dressing up as fancy as I used to but everyday I make sure that I look pulled together and presentable. My uniform is a nice Tee and skinny jeans with a cashmere cardigan and a scarf or necklace….even if I am just cleaning the house.

    1. @Bungalow Hostess, You’re welcome. I believe you are more comfortable with ladylike than I am – I could never wear a scarf in the house, I’d throw it off in an instant. What matters is it works for you.

  16. Only if a piece has especially good memories will I keep it, like the pink long sleeved wool gab dress, zip up the front, moderate shoulders, cuffs with great buttons, tailored. This was eons ago when it was ok to match shoes to the dress, or the bag, never both.

    I have a harder time parting with clothes from my daughter’s childhood…a closetful. And a few boxes.

  17. I’m minimalist. So I do like my closet clearly and do not hold on sentimental items.
    My daily uniform is almost the same like yours.
    But living in a cold clime for about 8-9 month a year does make it more difficult to get this kind of “look”. It’s much more nicer if one can wear Tees instead of Sweaters and Sneakers instead of Boots.

    I would love your post about your choices if you didn’t live in SF!

    1. @Barbara, Oh boy, let me think about it. So much of what I write here I am only able to say after the fact, i.e., I lived it first and then I analyzed it afterwards:). You have to wear boots, wool pants, hat, scarf, gloves, and I remember that layers were a pain the neck when going back and forth between indoors and out. Hmm.

    2. @Barbara, I do SO understand. Unfortunately one cannot replace the stuff 1:1, Cashmere V-Neck, T-shirt underneath, Jeans and Boots doesn’t look half as good. Maybe very extraordinaire booties (flats please)would do the job?
      Outerwear, Hats & Gloves aren’t the problem. If it’s cold enough you have to wear those puffy coats and yes, we all are Michelin Man.
      But I resist to wear wool pants, too conservative and scratchy:-).

  18. Great post – thanks for sharing your process! I do have some sentimental items – either things I wore for special events, or items that were generous gifts from family for the most part. I try to keep the sentimental piece population small enough that it stays in a particular part of the closet, though, so I don’t end up with loads of clothes but nothing to wear. I do intend to wear a couple of the sentimental pieces again, but they tend to be fancier items and thus I have fewer opportunities to use them.

    1. @Murphy, Thank you!. Yes, I keep the sentimental stuff in one place too. And some of it may yet be cleared out. So true that the sentiment is often for special occasion gear. I used to have a pair of overalls from the 1970s:). but I eventually threw them out.

  19. I keep the beautiful navy pinstriped suit I wore when I got married in 1996. I’ll never wear it again, as it’s out of style and no longer fits, but I can’t bear to get rid of it. There are lots of other things in my closet that I will never wear again, and those will go on eBay or be donated to Goodwill.

    1. @Sheila, I think a reasonable effort to keep one’s closets clear is sufficient. And clothing donations and sales are good for society and for the planet.

  20. Oh… I’m with ya sista. Purged my wardrobe a year or so ago. Then did a whole lot of re-purposing…can these pants that I wore to work with these shoes and jacket look okay with sneakers and jean jacket? etc etc. It helped that I started this two years before I retired…by consciously NOT buying “worky” things. The great thing now is that I only have to think up two or three (or sometimes even one) presentable outfit a week. One retirement must…a couple of really great coats for winter, since that’s what most people will see me in when I’m out and about.

  21. I like how you have sorted and organized your retirement wardrobe. I believe you are ready for anything and everything each day brings, and can dress up or down, yet always comfortable (except when you wear the scratchy one), haha! I can picture you waking when rested each morning, relaxing on your sofa with your computer and a cup of tea. Books are for later in the day, right?
    I have quite a few items with emotional significance from days gone by – a cream silk suit worn to a Rose Garden proclamation signing by President Reagan, and a plum paisley with purple suede waist yoke dress I picked up at Filene’s Basement. And a couple of items just to look at how thin I was at one time.
    Comfort is the key – especially shoes.

  22. What a great post!!! This is very difficult- the comment about kitty cat teapot shirt had me crying it was so perfectly true!! Arrgh.
    My rule is :
    If you havent worn, thought about or seen it in a year, out it goes.
    OUT. No matter what.
    I live in comfort now, close to slob…but sometimes I feel this age group I am in, especially not coloring my beautiful gray…..I am invisible until people know me. And I am selective where I get spread around to nowadays…..No excuse to be a slob. I dress for me!! I like it!! I like to look nice, put together, determined to be classic and surprising people (esp my peers) at how I DO NOT follow what a retired lady looks like, my gray hair is shoulder length, the lack of trendy gidgits just show them how silly they look dressing like a 25 year old…… :)

  23. have decided since moving to london that i have aged out of wearing shorts. they just feel wrong now + overly casual.

    and time marches on.


  24. Lisa,
    Thank you for this thoughtful post. I do have a few
    dresses that I no longer wear, but felt spectacular when I wore them,and my father’s old cardigan( he died 1975).

  25. love this post! Love the Issey Miyake top and the gold skirt. I missed my work clothes when I was on maternity leave! People are always curious about me working and say crap like “oh I’m lucky my husband has a great job and I can stay at Home” (???!!!) and I always think to myself (apart from so could if I was bothered) but where do you wear your CLOTHES????

  26. Hello Lisa,
    Long time reader of your same age, recently retired from the pc hardware industry, so I know from whence you speak. In a way, it has been fun to re-purpose the existing wardrobe items to suit my new life. For example, I now wear my grey wool pencil skirts with fabulous turquoise cowboy boots and get compliments every time I venture out. Learning about my hidden Artsy Cousin has been a revelation, a plus now I am on a much more stringent budget for clothing.
    As for sentimental items-only my wedding dress, as I read somewhere that to keep those older items of clothing meant one was hanging on emotionally to one’s past life.

    1. Pencil skirts and cowboy boots – go you! And yes, I may be hanging on emotionally to my past life, but it feels like it’s been worth hanging on to, as though I am all the years of my existence at once. If that makes sense.

  27. The retirement wardrobe posts are fun to read though far removed from my own life. I worked three days a week (12 hour shifts) most of my career and wore a uniform when I did, so I always had to have regular clothes for when I wasn’t working. I didn’t have to buy anything extra or even think about it when I retired.

  28. With the exception of my wedding dress, I got rid of the sentimental clothes ages ago. Now that I’m retired though, I’m faced with what to do with the really good dress pants and dresses. I don’t think I’ll ever wear them again but who knows. In the meantime, I need something more than jeans and T shirts. And what to do with all those cotton shirts that require ironing? I’d send them to the cleaners before but I don’t know that I want that cost either. Probably, in time, I’ll figure it out.

    1. @Bonnie Dicks, I have found that anything I wore for work that is fun to wear out, I’ve kept. The cotton button fronts, however, not so much. But I’ve been retired for 2 years and am only just feeling like I have it sorted out. So much is tangled up in the clothes, identity, agency, etc. I bet you’ll figure it out sooner than I did:).

  29. I’m late coming into this discussion! Lots of good ideas…but I haven’t seen reference to “quantity”! I’m in the northeast, where we deal with the change of seasons. I’d love suggestions regarding the number of pairs of slacks or capris for warm weather and the number of pairs of slacks for the winter. I often wear sweatsuits (the pretty ones, not “hoodies”) when I’m home or just grocery shopping. But how many pairs of jeans, black slacks, navy slacks, etc., should I have? I was always an “outfit” person but have changed to wanting fairly neutral slacks with multiple tops. Is it better to have fewer options and have to replace them more often…or more options so that each “bottom” lasts longer? I guess this becomes a personal choice, but I’d love to see comments!

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