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.)

The Perfect Pair of Jeans Update

So, my dress-wearing friend asked for an update on how things are going, a few months into my ThredUp /more skirts experiment.

And the answer is: good! Good enough to not know for sure which jeans fit me at the moment, and good enough to make another order from ThredUp, although I’m not yet ready to make the leap one blogger I admire did with No Pants July. (After all, even getting my white legs out in shorts is a bit of an accomplishment.)

Bear with me, I have some photographic evidence, self-timer and/or random relevant snapshot style:

top, Abercrombie, yard sale find by my mom; eShakti skirt from ThredUp; Scout’s romper from Goodwill

Above is a normal weekday for me at the moment. I love that this skirt is high-waisted and that it’s pretty long without being aggressively modest.

Here is a terrible shot of my favorite dress, as I’m stripping Scout from her onesie on her birthday for the cake eating bonanza.

Through ThredUp, I received my current favorite dress, the shirtdress above, originally from Theory, which arrived new with tags. I save it all week for whichever day I’m most excited about — it’s lightweight, green (my favorite), comfortable and pretty. I should probably iron it (at least the belt) but I don’t. So there.

When you realize the shirt you ordered is almost identical to your three-year-old’s

Above is one of the two dress shirts I ordered, the other being a workhouse of a white shirt. I don’t wear either much right now, except to church, as it’s been plenty warm without AC.

Recently I made my second ThredUp order, trying to fill out my wardrobe for the transition to autumn. I belatedly bought a maxi skirt, which is exciting (no shaving!) and also worrying (I’ll trip!). It’s my first maxi skirt since I overdosed on them in Uganda in 2008-9, where they were effectively mandatory. I also bought two new dresses, a turtleneck, two long sleeve t-shirts, a tank top, a short-sleeve button down, two medium length skirts, and, most excitingly, a brown-and-black J. Crew cardigan that is an exact replacement for one I found years ago at a Boston Goodwill and loved right into the grave last winter. All this — 11 pieces — came to $80.45 with free shipping. The most expensive piece was $20.70; one skirt was $.90.

ThredUp definitely isn’t for everyone; back when I had more freedom to try things on at stores, I probably could have gotten lower prices through Old Navy clearance and thrift stores. The really low priced items at TU can’t be returned, and free shipping has a high requirement, which is why I can only imagine using the site once a season or so, when I can swoop in and make a big purchase. As I mentioned in my previous post, the search features lack the granularity I want, so I find myself hesitating to shop for sweaters when I don’t know if they’re washable, for instance, and growing frustrated that I can’t search for shirtdress, etc.

Still, it’s excellent as a one stop shop, and seeing all my items together helps me think about combinations and reigns in my flights of fancy. It rules out my tendency in thrift stores IRL to grab the thing I love the best, or that fits the best, without considering what I’ll wear it with — this summer I’ve impulsively bought two dresses at Goodwill and they’re both a little shorter than is comfortable. I also feel like I’m getting better quality (J. Crew, Gap, Banana Republic, Ann Taylor in this order) than at Target or Old Navy, which are my normal sources for new clothes. Plus, it’s intoxicating to watch the site keep track of how much you’re “saving” (with this most recent order, $434.61).

If you decide it’s something you want to try, maybe think about using my referral link? (You’ll get $10 to spend and so will I.) If not, tell me what your strategy for clothes buying looks like at the moment!

The Perfect Pair of Jeans

Two springs ago, something amazing happened. My husband walked into a Gap in Cambridge, wandered around a bit, bought a pair of dark blue jeans in which he looked very handsome and…has never bought another pair since.

That’s it! He has one pair of jeans, and they always look great, and he hasn’t had to buy a single other pair. In two years.

Can we talk about all the reasons this would never happen to me? For one, duh, in that period of time I’ve swung about forty pounds in weight — even just during extended breastfeeding, I move from marshmallowy to wizened. For another, I’m pretty lucky to get two wears out of a pair of jeans these days before washing them is Absolutely Essential — and that’s if I play a little fast and loose with the definition of clean. And don’t you dare get me started on maternity jeans (a contradiction in terms, I begin to think).

Like half the Internet, I’ve been interested recently in the concepts of uniforms and capsule wardrobes. Post-pregnancy this time, I‘ve tried to streamline my wardrobe(s), choosing neutrals instead of always opting for the most rainbow-y item I can find at the consignment store. I’m also trying to channel my husband in seeking out exactly the right item, instead of settling for cheap and so-so.

Easter friends: One of Meg’s lovely new dresses; literally the only dress of mine that fits, is appropriate for warm weather, and is nursing-friendly

More and more, though, I begin to wonder if we’ve got the wrong idea, especially when it comes to mom jeans. The thing is, my figure has changed in such a way that jeans — especially the low-waisted stretchy monstrosities I once favored — aren’t ever going to work, and it’s not because I’m delusional about my size. A friend of mine with kids (pictured above) has decided to invest instead in dresses, and I’m intrigued.

The idea feels dangerously retro, but then, I’m the one actively pursuing excellence in housewifery. And I have been moving in the last couple years to more and more skirts and dresses — I spent as much of my second pregnancy as possible in dresses like this one, and didn’t have the droopy drawers problem of maternity jeans, and postpartum, I wore a lot of elastic-waisted skirts so I didn’t have to buy shorts (ugh) in a temporary giant size (double ugh).

So as a lark on Mother’s Day, a day when I’d worn a t-shirt and a skirt that straight-up doesn’t fit to church, while I “watched” 11,000 hours of Mighty Machines with poor sick Pippin, I decided to see if I could find a new, inexpensive wardrobe of dresses.

I started at eShakti, where Meg and I found both of the above dresses, but that meant I could only afford a dress or two, so I switched to ThredUp, which sells secondhand clothes, and developed an exhaustive list of criteria: button-down (for nursing); A-line silhouette (for belly reasons); cotton or cotton blend (because I’m slated for a sweltering summer); machine washable (because duh). ThredUp doesn’t have the granularity to search by terms like “shirtdress” or by fabric, so the hardest part may have been closing tabs on beautiful, impractical silk dresses.

Eventually I ended up with two dresses, a skirt and two button-down blouses J helped me choose. I hope they’ll work for both church and everyday wear. I’ll let you know how it goes, but don’t expect a lot of fashion blogger shots. Inevitably they end up like this:


I’m still on the lookout for the perfect pair of jeans, of course, but I begin to suspect that the perfect pair of jeans for me, for now…just might be a dress.