I Dressed Like Me for 10 Years: Day 1

What’s this? Here’s what! But TLDR, clothes, aging, bodies, media, feelings.

Something I didn’t totally figure out for myself before putting out the sign-up link for this newsletter was relationship between whatever’s in here and me getting dressed. I knew the series would probably be thinkier than the story I wrote in 2015 (also, not basically all made up), but should I still include what I wore each day? If I did, what would that mean for the clothes that go on my body? Would I get really weird about it?

I answered that for myself this morning when I threw on the sweatshirt and jeans in closest to my bed, grabbed a shacket I only bought because I thought it was a big shirt, and stumbled outside.

Since I stopped having a regular job, I’ve made it a rule that I need to be taking a walk by 8:30am, for structure and sunlight. I used to get up at 8:58am, so this has not been an opportunity for looking cute; it has been an opportunity to find out which of my sweatshirts still fit. (Sometimes it’s an opportunity say “fuck it” and go out in one I can’t get back off.) Tellingly, none of this has meant my daily wardrobe is any worse. It’s been about 5 years and 8 months since I (mostly) stopped getting dressed in the morning and just started covering my body. Since 2020, I might put on an outfit for an evening, or late afternoon on a weekend, but before the noon the whole game is obscuring nudity. The key is usually big shirt.

In my closet at this moment, I have four tops from the Gap that are part of their official “Big Shirt” offerings (available in organic cotton poplin, organic cotton oxford, denim, ultrasoft denim, corduroy, sheer organza, and “GapStudio,” which apparently means recycled polyester). I have five more in a digital cart on which I am trying not to press “check out,” because of the whole “no job or place to go” thing.

The appeal of the proverbial big shirt is even more vast than the shirt itself. These are boxy long-sleeve button-downs that politely refuse to notice when my weight fluctuates; they can be worn alone, poking out of sweaters, or, most frequently by me, unbuttoned or partially so over a tee shirt or tank top. They’re able to communicate messages like “hello, I’m dressed” or “wow, this woman thought to bring an extra layer" or even “love handles? I don’t think we have those here!”

In addition to Gap’s selection, I own three giant button-downs from Madewell¹ , one overlarge guy from Target’s Madewell knock-off, and three of what Sézane calls their “Max Shirt,” which we simply have to assume is French for “big.” These Sézane tops share a similar shape to the mall brands, but are $125 to Gap’s $41² to $98³ options, and two of the three I own are denim in slightly different shades, with snaps. That is goof troop ass behavior on my part. That is $250 (plus tax!) worth of the same thing, a thing that doesn’t even have the dignity of buttons.

Unfortunately, these jean shirts have become sartorially and emotionally load-bearing for me. If I’m a video game avatar, I am 100% bobbing in place in an oversized blue button-down. They’re the cornerstone of feeling like myself these days.

I bought the first, the lighter denim, almost by accident in summer 2024 after I braved the Soho shop hoping to try on a more formal, blue-white-pink striped cotton version⁴ with actual buttons that I’d seen on a chicer friend.

I appreciate plenty of things about my appearance when I’m like, at home, but I don’t tend to feel amazing in stores. I’m 5’1” and clinging on to mainstream sizes with tiny, unmanicured hands and an XL belly and boobs. Most designers aren’t particularly compelled by my measurements, so everything is long and tight and nothing buttons. Worse, Sézane doesn’t even call its retail outlets “stores;” they’re L’Appartements, which for my money should sell croissants or at least house French people. Everyone waiting in the line out front has smoother hair than I do, and I’m paranoid when that they see at me and think, “Aww, well, maybe she can buy a necklace!” I’d been inside once before for the same purpose, but bolted when I didn’t immediately see what I was looking for, lest anyone accuse me of wanting anything I couldn’t or shouldn’t have.

Returning, they still didn’t have precisely the thing I’d come for, but the saleswoman gave me the pale denim to try for size. I feared she’d purposely handed me the training wheels version of what I wanted⁵, but on, it was soft, drapey, insouciant but still composed. The snaps? Genuinely satisfying to snap. I bought it, unsure of the proper occasion for a decidedly casual top that cost as much as half of the dresses I’d ever owned.

It turns out the proper occasion was absolutely everything, which I think is correct. I had to get out of my own way about this, but if you’re going to spend a bunch of money on something that looks like it’s for everyday use, you should probably wear it every day⁶. I’ve worn it buttoned up in fall, layered under sweaters in winter, tossed in a bag for chilly movie theaters in summer, employed as an umbrella in a springtime emergency. I wore it enough that I ruined it with some kind of grassy, bleachy stain I don’t remember the cause of. That prompted me to buy the darker wash version, which is perfect, and which I will eventually destroy.

The ruined version — which frankly still looks great to me — is what I put on after forcing myself to shower, for my first full day of freelancing⁷.

Here’s my outside look: Sunglasses from Amazon, Racked sweatshirt (size small, ouch), blue corduroy “shacket” from Madewell, Curvy Perfect Vintage Straight jeans also from Madewell, Blundstones. Phone is wearing “Ben Affleck smoking a cigarette in a mask.”

Here’s my inside outfit: Sézane Max shirt in very light denim, Gap cropped white T-shirt, Gap “Mid Rise Easy Horseshoe Jeans,” socks (unknown).