Do you prefer 'fashion victim' or 'ensembly challenged'?

Note: this was originally published in Weighted Tangents, my Substack newsletter, which you can subscribe to here.

I have been fashion-challenged my entire life. It’s not that I don’t know when something looks good, I do! It’s that I have never, in the history of my life, been able to put together an outfit no matter how hard I try. I’ve copied what I’ve seen others wear, asked friends to help out, and even tried services like Stitch Fix, but outside of gym clothes I’ve never found anything that makes me feel like me. Instead clothes have always felt like some kind of costume I’m forced to wear in order to fit in, rather than an expression of my identity.

In the autumn of 2019 though, things were different. I had landed my fancy job at Kaggle, moved in to a beautiful loft apartment overlooking the Katy Trail, and had been slated to give several keynote addresses at various conferences across the country. It seemed like the perfect time to move past my obsession with athleisurewear and start dressing like an adult.

Because I wanted to overhaul my entire wardrobe with the help of an expert, I decided to try out Nordstrom Trunk Club. I filled out an online questionnaire, scheduled an appointment, and stumbled into the showroom wearing baggy jeans, a t-shirt, and sneakers, wholly open to the experience but expecting very little. Almost everything the stylist showed me provoked a raised eyebrow and “I don’t know about this” comment, but I dutifully tried everything on and was summarily shocked at how good I looked.

I ended up buying everything. The stylist had built the wardrobe in a way that I could mix and match pieces, and I left feeling confident that I finally had the base layer to a functioning wardrobe. If you saw me at rstudio::conf(2020) you saw the most put-together version of myself that has ever existed. I was doing a full face of make-up, waking up an hour early to slightly curl my hair, exclusively wearing the outfits my stylist had pulled together, and I felt amazing.

We all know where this story is going. With the onset of COVID the need for nice clothes dropped to zero, and when I moved to Chicago three years later I sent everything from that Nordstrom trip off to consignment — many items with the tags still on. My wardrobe has steadily decayed from professional to business casual to athleisurewear before bottoming out at “what is the most comfortable thing I can find?”

In short: I wear soft, dark, and baggy clothing. It’s all that I own at this point.

You have no style or sense of fashion

I didn’t anticipate animation classes being the prompt to push me to buy new clothes for the first time in years, but it turns out that it’s incredibly common to “shoot your own reference”, meaning videotaping yourself so that you can better understand a given movement. Surprising none of you, I’m sure, it turns out that dark, baggy clothes are useless for this task — not that I didn’t try. My first reference video consisted of me plastering lines of masking tape all over my body to try and understand what was happening, but it was futile. I couldn’t make out simple movements or track what my arms were doing, and so I needed to invest in animation clothes.

So without further ado I present to you my masterpiece:

Not only am I rocking two different colors of socks, I’ve put a hair tie on each wrist and a headband close to the top of my forehead. I giggled with excitement when I found this striped shirt with spots, and even managed to snag non-black leggings with a white stripe running down the side of my leg. Honestly this is the most proud I’ve ever been of an outfit. I can track all of the movements I need, from how my hips and shoulders are rotating down to the tiny details of how I move my feet. I may not be ready for the runway, but I’m definitely ready for my next homework assignment.