I once tweeted that choosing my outfit for first dates always feels to me like dressing as a “cool girl” for Halloween. It’s a balancing act, crafting an ensemble that communicates aloofness I don’t actually possess. My natural inclination would be to wear a party dress and a hair scrunchie on every date, and not everybody is into that “goodie two-shoes on picture day” vibe right off the bat. So I often end up wearing a T-shirt tucked into a casual skirt, or – in an even more performative gesture of chillaxed-ness – jeans.
Jeans and I have a fraught relationship. I wore them in middle school because it was the done thing, and then matriculated at a performing arts high school full of weirdos who made me feel safe casting off my pants (…metaphorically) and slipping into dresses and skirts. These twirly garments refracted my internal sense of femininity into something externally clockable. When I tiptoed back into denim-land one momentous day in sophomore year, it was, characteristically, in the least chill way possible: with sky-blue skinnies and cowboy boots and pigtails, a caricature of a tomboy I wasn’t. I attempted to strut but mostly just slithered, nervous everyone was staring at my thick thighs and muffin top, now exposed by pants as taut as sausage casings instead of curtained behind a forgiving skirt.
I mostly eschewed jeans again until university, where social anxiety coupled with a more conservative environment (i.e. no more teens in tutus and combat boots en route to improv practice) made me feel pressured to conform – to “dress my age.” People my age were wearing jeans almost daily, so I gave them another go. This time they made me feel pleasantly invisible, blissfully unremarkable. I tucked the cuffs into Bean boots and spent entire winters that way, trundling to class and back home on snow-caked streetcars, sitting in lecture halls with coffees and bagels, praying no one would see through my denim disguise.
Now, at 27, I’ve finally come to view jeans as a comfortably occasional thing for me. It’s a relief not unlike downleveling a romantic relationship to a friendship-with-benefits that suddenly runs smoother than ever before. Recently I tugged my partner into a Madewell fitting room and almost ceremonially zipped and buttoned myself into a pair of high-waisted navy skinnies. The effect was instantly magic: I felt clued-in, cool, and curvy. “That denim isn’t your typical style makes it even hotter when you do wear it,” Matt told me later, once money and pants had each changed hands. “In your new jeans, I find myself staring at your curves for what feels like forever.” I had tapped into the casual confidence of People Who Look Good in Jeans, a club to which I’ve never quite managed to procure full membership but which I drop in on from time to time.