What makes something cool?
It’s a question that’s been persistent in the back of my mind lately. I’ve wondered about it when looking at street style photos from NYFW, or while watching films. I considered it for weeks while I planned what to pack in my trunk for a yearlong tour. I’ve been reminded of it again while talking to my castmates about what they’re wearing to our opening night party this week—each of them so different (and here is what I love about artists). And I have felt suspicious of the answer to it every time I consumed content on social media pushing the trends the fashion girlies are eyeing this fall: chore jackets, riding boots, a resurgence of the all-black outfit.
[I’d like to mention that “what makes something cool?” is not a present question when I am digging through racks at a thrift store (maybe the only safe place left to consider personal style), and pulling clothes to try purely based on instinct.]
I’ve been feeling a little overstimulated lately, a little distrustful of my own taste—influenced as it is by the notorious algorithm. In response, my outfits are becoming simpler. I wonder if I’m tired or creatively stuck or both. Or am I, alternatively, on to something? Should I blame this new city, the cultural shift of my temporary home?
Looking around my corporate apartment in Chicago, I take in some of the clothing I have brought with me, the items that signal that I live here. A berry-colored, oversized suede shirt hangs on the back of a chair. A deep blue vintage bag sits on the dresser nearby, next to a trio of baseball caps. Inside one of those dresser drawers, the middle one that refuses to close flush, are pairs of thick socks, bike shorts, and a stack of soft, oversized tees. On the nightstand rest my watch and two rings. Hanging in the shower, one bright red swimsuit. And by the front door, in a short row, are some shoes: a blue pair of tennis shoes and a black-and-white pair, my loafers, some ugly-but-lovely black ballet flats (the French have a phrase for this), and the jelly flats I wear to the pool. I take in these things in a matter of seconds. I remember when I have worn them, and where.
What makes something cool? Fresh? How loud does an outfit have to be to qualify? How difficult to imitate?
I like the people I am with. In the dressing room, one of my castmates pulls out a bag shaped like a hardcover novel, that she will carry as a clutch to our opening night party. I love it, and I can see that she loves it, that together with her dress it will make the look hers. Another actor will be wearing a men’s workwear-inspired formal jacket. I tell him I can’t wait to see it, and I mean it. Others are wearing: a sheer dress, a deep green suit, a literal silver metal chest plate, a plunging neckline, white and gold feathers.
My castmate is telling the friend seated next to her about the maker of her new book-as-purse. People have carried book-like clutches before, but watching her show off the clutch reminds me of something foundational—that a great outfit first and foremost is a confident expression of the individual. There is an inherent looseness, a playfulness that comes with wearing pieces you love. It does not require newness or ingenuity so much as personal certainty. My castmate has told me more than once how painfully shy she felt as a child. Watching her now, to me, she is cool.