What I Learned Wearing the Same Dress 100 Days in a Row

I was having a jeans problem. This is my longest stretch in a decade where I haven’t been pregnant or nursing, and it’s also been a long stretch where brick-and-mortar shopping hasn’t been practical. Add that limbo to my long-standing and probably bizarre love of wool and my next sartorial move was obvious. In November, I used birthday money to get myself one of Wool&’s merino dresses, and in December, I started their 100 Day Dress Challenge. Here are some of the things I learned:

  • No one notices if you wear the same thing everyday. No one is paying attention to you, seriously.
  • I had suspended accessorizing during the baby era. Wearing the same dress everyday reminded me I could actually safely wear a necklace without someone wrenching it off, a scarf without suffocating my nursling. I’ve spent quite a lot of the last eight years partially undressing several times a day, but I don’t have to do that right now, and that spells freedom.
  • Tying the bottom of a loose shirt is my favorite way to create a waist on a baggy dress—not belts. Maybe it would be different if there were little loops on the Rowena to hold the belt in place on the dress, but inevitably my belts, even elastic ones, would shift and annoy me, or I’d find myself slouching to try to hold them on, and I definitely don’t need another reason to slouch. (On a related fabric-tying note, wadding up the dress into a little bun so I could wear it with jeans was easier than trying to tuck it in and fluff it up, even though the Internet says you can do this with dresses.)
  • I actually really like a baggy dress, though. I had never worn a shapeless dress before because I’m a pretty scrawny person and always felt lost without some tailored curves, but it really is incredibly comfortable to just hang out in a sack, and if it’s a pretty sack, what’s the big deal? People still know I have a waist even if it’s obscured in merino.
  • You can do anything in a dress. Granted, I wore leggings underneath nearly always, or else (wool) tights or jeans, but in my 100 days I biked and hiked, baked and cooked, taught and kept house, gardened and attended Mass. Many of these are activities that would ordinarily have had me changing out of the Dress either to protect the wool, or for more range of movement, or to keep me warmer, but I was able to work around it, and mostly enjoyed the challenge.
  • My girls are camera junkies. Endless photobombs, plus a lot of odd shots taken by my willing camerawomen.
  • I, on the other hand, am not. I used to be fairly comfortable in front of the camera in college when we were all just figuring out digital cameras and racking up tons of shots, but during this challenge, it was hard not to be embarrassed, especially on whole body photos, not because I’m self-conscious about the way my body looks but because I don’t know how to hold myself at all. (Also our house is really cluttered, I have found!) I’m hoping we’ll like looking back on all these ridiculous photos later, though, and remembering what I was like at 35.
  • There are things I can do to feel more comfortable in front of a camera. And with many of us still doing most of our socializing via Zoom and FaceTime, those things are worth thinking about. I can wear lipstick if I’m not about to don a mask. I can try to embrace my long hair, the legacy of the pandemic. I can replace my janky, cracking glasses. I can bleach my teeth, for heaven’s sake!

I don’t think you have to go the Wool& route to enjoy some of the benefits of simplifying your wardrobe and/or putting more thought into how you present yourself, but it was truly a fun project this long, dull, hard winter. And after 100 days wearing the Rowena dress? I’m not ready to trash it or burn it, and I think that’s a testament to its quality and versatility.

(This is a reflection, not a paid promotion. For interested parties, the dress did spring one tiny hole around Day 75. I washed it about once a week on gentle with Woolite and air dried overnight — I couldn’t do the recommended smell test for obvious reasons.)

9 thoughts on “What I Learned Wearing the Same Dress 100 Days in a Row

  1. what a fun idea! you’re so cute and stylish (and practical!)

    On Mon, Mar 22, 2021 at 10:05 AM Leave in the Leaf wrote:

    > Katherine Grimm Bowers posted: ” I was having a jeans problem. This is my > longest stretch in a decade where I haven’t been pregnant or nursing, and > it’s also been a long stretch where brick-and-mortar shopping hasn’t been > practical. Add that limbo to my long-standing and probably bizarr” >


  2. I have seen this challenge before and was interested to hear someone’s perspective. I love your dress too!
    I don’t know if you’ve heard of The Daily Connoisseur, but she does a 10 item wardrobe seasonally and I think that’s the route I’m going to go this spring/summer. When I’m home, I tend to wear the same three dresses over and over anyway!


  3. I love this. You look great! I’ve occasionally been tempted to do it myself but have chickened out. 🙂

    Also I have that book about Paradise Lot out from the library right now. 🙂


    • Thanks, lady! The unexpected advantage of doing the dress challenge is that, from early December to mid-March, I had a built-in countdown to this interminable winter…

      I really liked Paradise Lot! But I may have been somewhat biased because a.) it was right after reading a permaculture book I mostly didn’t understand but which repeatedly advocated peeing on your plants and b.) the plot was located in Holyoke, where I worked as a librarian for a couple years, in the area where we attended grad school. Bonus!


    • I love the concept of the Wool& company. I may consider one of those dresses. (Definitely would help with the decision fatigue of deciding ‘what to wear’ – while also encouraging creativity.) The idea (of knowing where the wool comes from, etc.) reminds me of a children’s book: A New Coat for Anna. I forget the author, but perhaps you know it already? It’s a lovely children’s book. Thanks for sharing about the dress.


      • I really enjoyed the experience, and I’ve got my eye on a dress from them that might work in summer (or at least milder weather) to use my gift money on. I like knowing where my clothing comes from, too — well, actually I just usually shop secondhand and then I don’t have to worry! I don’t know that book but it sounds right up my alley. Thanks for the recommendation, I immediately added it to my library holds 🙂


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