Podcast: What do you wear — and not wear?

Back in a different phase of my life, I used to watch a lot of episodes of What Not To Wear. In the show, the hosts would go through a person’s closet, and toss almost everything as being too old, unworkable, unflattering, etc. They would then give this person (almost always a woman) $5000 to go purchase a new wardrobe, with guidance from the hosts about what worked and didn’t.

I found the idea of building a wardrobe rationally, and all at once, so you were looking for combos that worked together, appealing. (The professional styling advice would be nice too!) I think a lot of other people do as well, which explains the perennial popularity of “capsule wardrobes” — the idea of having, at least for a time, only a small number of things in your closet, and only things that you actually wear.

(Real Simple, for instance, runs a story along the lines of “5 items that will take you through the whole work week” approximately every other month. M.M. Lafleur had one of their staffers write about wearing a mere 5 items to work for the whole month of November).

So Sarah and I were excited to welcome Courtney Carver to Best of Both Worlds this week. Carver is the author of the new book Soulful Simplicity, and she runs the website BeMoreWithLess.com. She is the creator of Project 333, which encourages people to choose 33 items to wear for 3 months. Box everything else up. See what works, see what doesn’t. You’ll learn more about your style, and as you repeat the process, you’ll hone your wardrobe down to what looks great on you and makes you feel good too.

That’s important, because wardrobe stress has a cost — especially for professional women. Time spent getting dressed is time not spent doing other things: working, hanging out with family, relaxing. Mental energy spent debating what works each morning is mental energy not put toward solving your most important business issues.

Anyway, I’m not particularly a minimalist (Sarah finds the idea much more appealing!) but I do know there are items I wear over and over again, and also items I buy and then just don’t wear.

For instance, I’ve bought a fair number of skinny jeans because they’ve dominated the pants options in stores for the past decade. But the truth is, I don’t like them. I tend to wear straight leg jeans. Good to know that.

I also hate uncomfortable shoes. I’ve bought a reasonable number of nice heels for speaking, but then I found a pair (Clark’s) of bone-colored heels that are quite tall (there’s a platform under the toe) and that I can actually wear for longer than 2 minutes. So now I pretty much don’t wear any of the others.

Then there’s the cashmere sweater debacle. I like how they look and feel…in the store. Then at home they pill, and apparently we had moths in the closet because now all my cashmere sweaters have holes in them. Sigh. The winter tops I wear most often turn out not to have wool.

What have you bought — or kept buying — that you never wear? Have you ever tried a capsule wardrobe? What are your most versatile pieces?

40 thoughts on “Podcast: What do you wear — and not wear?

  1. I am a minimalist, and when it comes to my wardrobe, I STILL find that I end up buying things I don’t love … I am re-reading the Madame Chic books to remind myself that it’s OK to wear things over and over! This is what French women, the style icons of the planet, do 🙂 If I don’t love something I wear, it makes me feel “off” all day.

  2. I’m either the worst or best at this. I have a closet full of dark jeans – probaby 20 pairs, 8 pairs exactly the same size and brand, and about 15 black buttondown shirts. I have a couple of gray shirts, about 5 white and two blue. On the occasion I wear something other than the “uniform” sometimes people will complement the change, but when I see photos, more often than not I look best in basic black… One benefit – I can dress in the dark : )

  3. What not to wear was the best! I loved watching that show. The main thing I need to be realistic about is heels. I just need my feet not to hurt. Also dresses and skirts without pockets. I need to get rid of them, I never reach for them, when I have perfectly good dresses and skirts that ALSO have a place for my phone and keys. Can’t wait to listen to the podcast!

    1. @Ana- such great television. So satisfying to see someone’s life re-made in 42 minutes. And so body positive too. I mention in the podcast Stacey’s great line to one woman who was saying “well, I need to lose weight and then I can wear these pieces…” “Why would you lose weight just to wear ugly clothes?” I loved how people of all kinds of shapes would look fabulous with the right clothes and haircut.

  4. Ohhh, I loved WNTW as well!! I wonder if there’s something similar on these days?

    I love the idea of a capsule wardrobe but I still end up accumulating too many “good” items. It’s easy for me to weed out the “bad” ones, but then I end up with 3 pairs of black leggings, all of which I like, etc. So I need to tackle the shopping issue ;D

    I found it ridiculously stressful when I had to wear “nice business casual” to work daily – ie no jeans, only dress pants, no T-shirts, etc. Fortunately I’ve never had a job that required suits.

    Microsoft was my happy place – I could literally wear ANYTHING to work, including sweats or leggings/UGG boots. If I wanted to dress up, or was meeting customers, I could, but it was infrequent.

    I definitely have a “happy place” – a number if items in my closet where everything is great and it’s easy to get dressed in the morning. Right now I’m over that – it’s too many choices and then it gets overwhelming. We are in the midst of remodeling our master bedroom & bath, so when I move back into my closet (which I will now have to share with my husband) I think I’m going to try sticking to a specific number of items again. 33 is probably too small, but around 50 is great 🙂

  5. About 2 years ago I got rid of about 3/4 of my clothes. Since then I have tried to be very intentional and make sure that I only buy things that I absolutely love. There have been a few things that landed in my closet out of desperation, but for the most part I really love all the clothes I have.
    I have done stitch fix 5 times and while they did magically find me two pairs of jeans that really fit well, I haven’t had much luck other than that. Maybe I’ll try the Nordstrom trunk club.
    Great podcast today! I love listening.

  6. This was such an interesting episode! I used to buy tons of clothes that I ended up not wearing. I tried Stitch Fix and a few other programs. About a year and a half ago, I discovered the program called Dressing Your Truth. It’s a free online course that helps you determine what styles and colors you should be wearing based on your Energy Type (which I admit sounds very new agey but the results speak for themselves). Now everything in my closet goes together and I know how to accessorize and do my hair and makeup. I actually look forward to getting dressed in the morning now!

  7. Thanks for doing an episode about clothing! I’ve long enjoyed Courtney Carver’s website and books, and Project 333 has always been intriguing.

    My wardrobe is on the small side, although nowhere near 33 pieces. After having kids, I found the slim-hipped work pants weren’t so great anymore, so they went bye-bye. A few years later, skirts began to feel like a hassle (coordinating with tops! that always wrinkled! and always needed to be re-tucked!).

    So for the last several years, I’ve worn exclusively dresses to work. 28 of them, to be precise, all largely in the same silhouette: knee-length or just below the knee, very slim fitting, and with a v-neck or some kind of interesting, structural neckline. Add a pair of high heels in bone or black and an statement necklace or scarf, and voila: done! Dressing takes about 3 minutes when all your clothes are your favorites.

    The weekends are similarly easy: black or dark blue denim, about a dozen shirts and sweaters, and flats or booties.

    1. I love dresses too. Everything matches and you look pulled together. I haven’t counted my work dresses, but I would guess I have about 20 including both summer and winter and crossovers.

      SHU I just got 2 new wrap dresses from Boden! I have been shopping there for several years. I am not post-partum (my youngest is 2) but I still find wrap dresses so easy. My new favorite tip is to have a snap placed where is crosses at the neck line to avoid gaping when I bend over patients (eek!).

        1. I always used safety pins too. I always worried about them showing. I did a personal styling session at Nordstrom (like Trunk Club in person) and one of her recommendations was to have the snap put in. That means it is always in the right place. As soon as I get a wrap anything I pin it and send it out with the cleaning and it comes back with a snap.

          1. Double sided fashion tape works wonders too! Plus it’s removable/adjustable, for more or less va-va-voom as needed! 😉

      1. Ohh, the snap is a wonderful tip. Thank you for that! I have a dress I was about to give away because the safety pin annoys me. I’m going to try to sew on a snap first!

  8. I too wear the same favorites time after time, but I really feel happy when it’s time to change seasons and get out some different clothes. Remember Color Me Beautiful book? The premise of only colors that look good on me still controls my closet. The one thing I wear all winter that I dislike are black warm tights. I need the smooth warm layer, but the color options are pitiful.

  9. I shop almost exclusively at second hand shops so I take what I can find. (What appeals to me and fits on any given day.) At that price I tend to over buy but I’ve gotten much better at donating what I’m not wearing in short order.

    I also make a big percentage of my wardrobe (knitting tops, shawls, shirts and sometimes dresses). It adds a later of difficulty to coordinate the hand knit items as yarn trends don’t really mirror fashion trends and the colors (etc) can be off.

    I’ll be moving into a new bedroom and closet soon so I expect there will be a big culling. Looking forward to it!

    1. @Christina – interesting! I’d love your tips on how to shop well at second-hand stores. I would imagine, much like shopping for furniture and antiques and such that there is a certain art to it.

  10. I am horrified about what happened to your sweaters! Ack! Are mothballs still a thing?

    I feel the same about comfy shoes. I’d love to be able to wear heels but they hurt too much. I suspect that if I walked less i could wear them, but then… what’s the point of that?

    1. I do keep a few pairs of heels in my office at work for days when I have meetings or a few clinic patients but not rounding or being on my feet all day. And a coule of pairs at home for date nights where I know we will take a cab there and back.

    2. @Omdg – I bought some cedar blocks, and I bought these bags that are supposed to protect the sweaters, but I swear the moths still got in there. I put one sweater into a bag hole-free and it came out with holes! Very frustrating. I mean, definitely a first world problem, but still.

      1. You inspired me to look this up, since I have quite a few sweaters in storage: apparently cedar blocks don’t work. They recommend against mothballs but suggest nothing else that is effective. I bought mothballs.

  11. If cashmere doesn’t work for you, why don’t you try merino wool? They are not as soft, but are more durable and rarely pill. If not, you can still save your cashmere sweaters by darning.

    I do Jennifer L. Scott’s “10-item wardrobe”. It’s the easiest way to look good, while saving time and money, and get off the fast fashion wagon. The most versatile item I own are black pants. They go with everything! In summer, I wear mostly dresses because I’m too lazy to think about pairing.

  12. I have a uniform of sorts. I like fitted (with a little stretch) pants. I have them in black, brown, gray, navy, white, but also some olive and other colors for fun. Pair with tunic tops that usually have three buttons at the top and then are flowy through the middle. Shoes are flats. (Memory foam is my favorite.) Then during cold weather I add a cardigan, and the flats become booties. I rarely vary much from this basic uniform. I can dress it up with a blazer and heels or even dress down with converse and a t shirt.

  13. I listened to this episode today because I looove the idea of a capsule wardrobe and have been working towards that ideal since 2014, but my weakness for shopping and things like Trunk Club are causing me to accumulate more than I need. I am inspired to try Courtney’s Project 333, but I decided on 40 items through 3/31. I’m not sure what the weather will be like here in N CA since it’s my first winter/spring here so 2.5 months seems good for a first try. I made my list of items on paper, and quite honestly, the last few were difficult to fill in – around 35 I had covered everything I really love. I guess that’s my answer 🙂

  14. I spent an entire summer watching back episodes of WNTW, and it changed my whole perspective on dressing myself. I’m pretty happy with my wardrobe, which is not capsule-ized, but full of good quality pieces that I like. I have a sort of “uniform” for each season of professional and casual outfits, and when I’m stuck on a given day, I fall back on that uniform. But I do like getting dressed in whatever strikes my mood, so paring down and organizing further wouldn’t make me happier.

  15. I also wanted to recommend an *excellent* book for people interested in exploring their style and figuring out what *should* be in their wardrobe, along the lines of the questions Laura was asking Courtney Carver on the podcast. It’s called The Curated Closet by Anushka Rees and it’s extremely thorough and well-done. It makes wardrobe building a science, and it’s like an extensive textbook on the subject. If you don’t care that much about your clothes, it might be too much, but I loved it.

  16. I have two rods for my clothes – one for bottoms (skirts, pants, etc)/dresses and one for tops. I have to wear some combination of the first three items on each rod (ie the first pair of pants with the second top). After something is worn, it goes to the back of the rod, and can’t be worn again until I’ve gone through the whole rod. Once I get down to the last 3 or 4 in each section, I take a picture, and I can start again from the beginning.

    If something is in the picture more than a few times, I know that it just doesn’t work for me, doesn’t fit in with the rest of my clothes, etc., and I don’t feel as bad donating it. Non-seasonal and special event items are not included.

    This helps me put unique outfit combinations together, takes much less choice, stress, and time to choose outfits, and ensures I’m wearing everything in my closet.

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