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Shop Now For Your Future Retirement, Or, Part B Of The Thoughtful And Stylish Wardrobe

And now, some thoughts on how you might shop today for tomorrow’s retirement. Working, I used a fair amount of my salary to buy stuff for stress relief. I think one is allowed indulgence. But with a little forethought, that indulgence becomes investment.

What’s Gone?

Over the last 20 months since I stopped working I’ve gotten rid of a lot of clothes. Mostly those that were neither comfortable enough nor special nor enough “me” to keep.

The best of the last group I saved for my blog sale. Thanks everyone!

Then off to the American Cancer Society went Monique Lhullier, Giorgio Armani tunic and pants, a shiny raincoat, Toast jacket, some Stuart Weitzman net pumps and several pairs of Beautifeel shoes. To Goodwill I brought J. Crew bootleg corduroys (bootlegs have to be fitted to look good, so these were neither comfortable enough for staying in nor edgy enough for going out), a black Costco peacoat, numerous t-shirts, and lots of exercise clothes and casual shoes.

What Did I Keep In Retirement That I Bought For Work?

From my last office, which was very casual, I have kept two Isabel Marant tweed jackets, a Dries van Noten dress, an All-Saints motorcycle jacket, Dickers boots, the J. Crew field jacket, and Gravati brogues. From previous, more formal offices, I’ve got a Chanel jacket, a Brooks Brothers button-front, navy linen Giorgio Armani pants, and a gray silk and wool Luciano Barbera pants suit. You know, in case I ever have to speak in front of a business crowd again.

If you’re still working, here are the type of pieces you might buy with an eye to retirement.


  1. If you never wear it on the weekend, you are unlikely to wear it in daily retirement.
  2. Office basics are not investment for retirement. Office “special” pieces however, if they can stand alone for a special occasion or dress up a casual outfit, are.

Just make sure that your investment pieces hit your your sweet spot in color and silhouette. I keep wishing I had the perfectly cut aubergine Marant jacket in black instead.

What I’ve Bought Since Retiring

  • Outerwear: Blue Max Mara jacket, white Costco peacoat
  • Shoes: Birkenstocks, both gray and white, Vince sneakers, brown and black New Balance for city walks, puffy pink and white Nikes for workouts
  • A Lotta Pants: Citizens of Humanity boyfriend jeans, white boyfriends, J. Crew drop crotch khakis.
  • T-Shirts: Costco white lace, Target b&w striped, Jigsaw gray and white stripes, UNIQLO lavender, gray, and white

Kind of like this.


  1. If you buy special pieces in your best colors and silhouettes while you’re working, you can play with t-shirts, shoes and other casual gear once you retire.
  2. Learn how to use jewelry and/or scarves, it’s a useful investment of your time.

On The Hunt

I’m now looking for pieces that are edgy, but not so much they require emotional bandwidth to wear. I want my clothes to up-level me enough that they don’t hang me out to dry. Always in Polished Tomboy. Tricky, work in progress. Ordered this, sent it back, too weirdly cut at the neck. Still looking for :

  • Comfortable yet sophisticated top to wear with drop crotch khakis, so I don’t look like a street denizen. Turns Jenna Lyons can pull off ultra-baggy, it’s a little harder for the rest of us. But they are so comfortable, (see Most Important) that I’m going to try.
  • Dark capacious casual jacket, with a modern edge. When I wear a black tee I don’t like to wear a light jacket.
  • Blue tees to replace the ones that have developed “jean button” holes at the waist.
  • Slides
  • Flannel pajamas in something other than Must Be PJs Plaid, or Breakfasts I Love Print. Finding jammie bottoms in a sophisticated ikat, or a tonal photoprint — anything that could make less evident that I’m my pruning front yard roses in sleepwear — would elevate my retirement style exponentially.

A few possibilities. Except for discreet flannel pajama bottoms because I’ve not found any.


None so far. Am staying in the moment where lessons are lived as learned.

Note that affiliate links may produce commissions. Part I of this series is here. You may also be interested in this Already Pretty post on comfort.

32 Responses

  1. Not sure if you’ve looked but I’ve a few La Senza flannel pjs that I like. I also bought a few from a store in Perth, which for the life of me I can’t remember anymore, inexpensive but ones that turn out to be most worn.

  2. I am enjoying reading about your casual tomboy wardrobe…Bed Head make great flannel pj’s…at least I think that’s what they are called! Dani BP Mop Philosopher is related to the owner and she wrote about how great they are…I am still having those nasty night sweats from menopause so I dare not even consider trying a pair!
    It’s going to be a scorching weekend here so I am dressing in cotton….living in California I can visualize you wearing a kaftan at dusk while you hand water your garden :-)) perhaps I am romanticizing.

    1. @Bungalow Hostess, You’re so cute! I hand water in my flannel PJs, usually in the morning, but yes, sometimes at twilight:). Oh, and I don’t actually SLEEP in my PJs, just put them on when I get up!

  3. Bungalow Hostess you’re right the company is Bedhead and the owner Renee Claire Bertrand is my cousin, good memory! Lisa I checked out the site and she does sell separates now (I believe at one time the pajamas were sold as sets only)
    I have many pairs of the pajamas and they are the best, the drawstring is always done perfectly and the fabrics are to die for. I also own one of the cashmere robes and I adore it.
    Renee Claire manufactures everything in Los Angeles, she really runs an amazing business and she designs the prints as well. Check it out (and I think there’s a 15% code on if you do a Facebook Like).
    I’ve enjoyed these posts Lisa, your thought process is always so interesting.

    1. @DaniBP, I have a pair of Bedheads – and the flannel is very nice. However, the bird pattern, as gorgeous as it is, clearly says Sleepwear. I don’t suppose you might ask your cousin if she’s ever thought of using different designs? I keep thinking of the Block Shop, and the printed scarves they have done in Rajasthan. If I could have Bedheads in block prints, with the subtle palette, I’d be in heaven. It’s possible I’m not the only one:).

    2. I would love some in block prints as well. I wear a lot of Bedhead PJ’s, also not for sleep, but for lounging around

  4. I’ve been “retired” for many years. First, I was a middle school history teacher (don’t even ask about that wardrobe) and then a mom at home. I have NO IDEA what I wore during the mom years. I truly do not remember. I was running here and there–making sure our boys were well dressed as well as my husband–with no thought about myself. Typical mom.

    These days, living in both a big city and the rest of the time in a rural area, my wardrobe has two distinct personalities. In the city, I wear mostly dresses—easy dresses–but dresses nonetheless. I favor Eileen Fisher knit midi dresses–mostly sleeveless in warm weather, sometimes a cardigan thrown over. At the rural homestead–anything goes. I don’t wear pajamas, but workout clothes have been known to reign supreme. Basically it boils down to whatever is comfortable. A trip into town will merit a change into one of my dresses. Scarves, necklaces, bracelet, rings–are all part of my simple ensembles.

    It’s all about dressing easy and comfortably–but hopefully tastefully.

    1. @Susan, That sounds perfect. If you are comfortable in dresses – and I do think they are best for heat and humidity, seems like you have this sorted. Now, I can only suggest, no harm in a splurge now and again;).

  5. I think shopping ahead of a major lifestyle change like retirement might be risky. You just never know what will happen and then you’ll be giving away things you bought because you thought they’d fit your lifestyle or waistline, and it didn’t work out that way.

    I think I’ll focus on purchasing items like cars, refrigerators, whatever while still working and let my wardrobe slide until I was actually retired.

    1. @RoseAG, I might have thought the same, but it turned out, in my case, that those things I always liked to do, i.e. dress up for events and for dates, I continue to enjoy, and the clothes transitioned if they suited those activities. It was the clothing that only worked for work that ceased to work in retirement.

  6. Lisa,
    I’ve really enjoyed reading about your experience and thoughts on a retirement wardrobe. I retired two years ago and at the time I had two types of clothes, those I wore to work and clothes suitable for the grocery store on the weekends. I told my work colleagues that if they saw me in yoga pants out and about after retirement to do an intervention. I think I was worried that if I didn’t have a reason to dress properly, I wouldn’t.
    After two years I have built a wardrobe that works quite well, a uniform of sort. I have purchased new jeans but not all are denim. They include dark wash, black, khaki and white. I shop for tops at two stores, Nordstrom and Target. A Target Tee is perfect for a cleaning, cooking and gardening day. I have some Eileen Fisher tops and sweaters that I think look very smart and take me to lunches, the movies and volunteer jobs.

    I was very surprised to find that I wanted a whole new shoe wardrobe. I thought my feet grew, but someone said the actually flattened out. So I’ve donated or tossed almost all my shoes. I’ve tried to find comfort and style in my new shoes and found that I’m happiest when I spend a little more.

    Another surprise was when I realized that the nice dresses and suits I saved from my working days where like old ladies hanging in the closet. I recently was honored for volunteer work at a special dinner. I went to a nice department store and found a dress marked down. Wearing a new dress to the dinner made me feel stylish and special.

    1. @Patty, Sounds perfect. My clothes are becoming a uniform of sorts too – but in retirement I’m clearly exploring the Artsy Tomboy side, so it’s taking me a while to figure out a newly adventurous style. BTW, I’d love some black jeans;).

  7. I didn’t think I could like you any more than I already do, but this sentence did it for me: I’m my pruning front yard roses in sleepwear

    Stars. They are just like us. :)

  8. Funny, I’m the same about a black tee. Only will wear a black jacket or a denim jacket over one. Not sure what type of top you’re searching out for the khakis? Something very casual, or something that you could go out to dinner with them in? I like khakis with a slouchy white silky blouse. Very “Out of Africa” and Katherine Hepburn-ish.

    1. @kathy, I like the Out of Africa look too. In this case, the drop crotch is so eccentric it’s hard to wear a tee with, so I’m looking for a cotton top with a little eccentricity of its own. Yeah, I’d wear a denim jacket over a black tee too. I’m sure there’s a scientific reason but I don’t know what it is!:)

  9. I own several pairs of flannel pajamas too, all plaid except for one pair of plain black ones. Unlike you, because I live in a cold climate, I do sleep in them. Hope to see a future post on grown up ladies jammies soon!

  10. Thanks for these retirement wardrobe posts! I’m working on what will hopefully be my final round of deciding what to keep & what to donate since retiring several years ago. The things I’m keeping are starting to help me figure out what I need to buy to make it all work together. For instance, I’d been thinking it would be nice to have a teal blazer. Then I realized I really like how my several Pendleton jackets go with jeans or skirts, & their classic style has stood the test of time, so I bought a vintage teal wool Pendleton blazer on Etsy the other day & I love it! I’m having fun trying to figure out my style persona, which seems to be something like tailored cowgirl.

    1. “Tailored cowgirl!” And do you have any buffalo check Pendleton’s? I’ve always loved those.

    1. :) I tried cheap ones at the GAP and had to run away fast. But if any exist in 100% cotton, yeah baby.

  11. Hi Lisa, no buffalo checks yet, but now that they’re on my mind I’ll probably see them everywhere! I’m hanging my head sheepishly because I’ve always called it “buffalo plaid” even though it’s clearly a check. Speaking of sheep, I just had a look at a website showing different plaids & checks & had fun seeing the “shepherd’s check”–I didn’t know it was called that, or that it is so-named because Scottish shepherds wore it, & it’s a precursor to houndstooth check. As Skippy & I are learning to herd sheep, I loved the names of those checks!

  12. Love these posts. I have been eliminating and parsing as well, but you write about it much more clearly than I can imagine doing.

  13. Recently retired from counselling, although I still do voluntary work – my clothes have always been “soft” and on the casual side, so didn’t have to get rid of anything. These days I concentrate on my Artsy Romantic doppelganger, and I love wearing maxi skirts (wool in winter, cotton in summer); fitted tops and cardigans; sometimes topped with a waterfall jacket or velvet semi-fitted blazer. All in gorgeous, glowing colours! Even for gardening and housework, I have long, faded denim skirts and tops in bright colours. I never wear jeans and haven’t for 30 years! And finally I feel I am dressing like me. New additions are similar garments in top quality fabrics, and everything goes together nicely. Feels like fashion freedom to me, although you could say I’m an eccentric Englishwoman, and that’s fine too.

    1. @Elizabeth Ann, This is so excellent! Talk about fearless living! If you can even garden in maxiskirts, you’re fully authentic across the board. And enjoying yourself.

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