How to be Cool

"Coolness is not innate. It is made from a series of choices."

Good morning! I hope you are all safe and well.

No ADHOC categories this week because I wrote another essay. This one traces the origins of Ivy League style and attempts to untangle the meaning of cool.

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Before cool, we should start with Ivy.

I learned listening to Articles of Interest that the Ivy style was born on undergraduate campuses in the 1920s—at Princeton in particular. The college had a large cohort of student-athletes who wanted to easily transition from polo practice to dinner at the eating clubs. They favored collared shirts and trousers to full suits. They were unbothered by scuff marks or tiny holes. In 1965, four Japanese authors published Take Ivy, a book of candid photographs taken on Princeton’s campus, as a sort of anthropological project.

Images from Take Ivy.

The boys look relaxed, casually suave. The way that they dressed was representative of northeast Ivy League colleges: sporty, simple, put-together. It’s unsurprising that even now, echoes of their style are omnipresent. Many of the pieces that constitute the Ivy look are now considered “normal” clothes: button down shirts, khakis, loafers, blazers. In the early years of Ivy, it was contained to stores like Brooks Brothers and Ralph Lauren, but now you can find it anywhere.

Although WASPs originally wore Ivy, it was Jewish Americans who built the apparel brands that sold the clothes, Black musicians and activists who adopted and adapted the style, and Japanese businessmen who were active agents in its proliferation and permanence amidst ever-quickening trend cycles. Counterculture transformed Ivy into the more mainstream “preppy,” and the way that elite college students were dressing in real life became something that the general public could participate in.

Ivy League colleges are beginning to diversify the classes they admit. As of 2024, white students make up only 41% of Princeton’s student body. But it is difficult to wipe away the origins of Ivy and the lifestyle it is associated with. The racially-diverse cast in the 2021 reboot of HBO’s Gossip Girl, dressed in “school uniforms” of designer blazers and pleated skirts, doesn’t feel as believable as the original, all-white 2007 series. One, the idea of Ivy is still tethered to old money, New England elite. Two, the effortlessness of the aesthetic is a primary reason for its appeal. We adore Serena van Der Woodsen, with her half-unbuttoned white dress shirt and tie loose around her neck, for her clumsy, ineffable luckiness. Things work out for her, regardless of whether she deserves it. The new cast looks stiff and costumed, wearing boots fresh off the shelves instead of scuffed from high school parties. The actors could have been plucked off of my Instagram explore page and plopped onto the MET steps.

Gossip Girl, 2007 vs 2022.

I went to the same NYC private school from 1st to 12th grade. We wore navy and white uniforms until 5th grade, when we graduated to a “dress code” that allowed colored collared shirts and any pants that weren’t blue jeans. In high school, the rules loosened even more, and we could wear whatever we wanted, as long as it was modest and inoffensive.

Many of the girls in my grade formed a magnetic attachment to Brandy Melville, the Italian brand that sells affordable, one-size-fits-all women’s clothing to a predominantly teenage audience. They lie somewhere between preppy (cable knit sweaters, collared shirts) and Southern Californian (tank tops and floral dresses). Most of Brandy Melville’s sales associates and models are young girls—white, blonde, thin, fresh-faced. Brandy sells a lifestyle of easy comfort and cool, but only if you inhabit a hyper-specific physical form. I recently watched the Brandy Melville documentary, and it confirmed many things I suspected were true. The exclusivity is on purpose. The employees are miserable. The leadership is problematic.

Admittedly, I still shop at Brandy Melville when I’m home for break. I take the train down to their flagship in SoHo to browse the garments on cotton-wrapped hangers. There is a specific smell, floral and musky and slightly sweet. All the customers are girls my age or younger. Often I’ll see someone I recognize from high school, and we’ll sheepishly smile at one another. What was a novel discovery in the fifth grade has become basic and ethically questionable. When I ordered my first package eight years ago, it came with thirty prints of promotional photos. I pinned them to the bulletin board above my bed, delighted that they had given them to me for free. 

The vibes of my old room decor. I replaced them with my own photos years later.

During the pandemic, I was adamant about showing up to Zoom class in a complete outfit. I’m not sure if I believe that fashion is a vehicle for self-expression or if I was simply resisting the strict, preppy clothing guidelines I had to follow for most of my childhood. It could have been a mix of both—I love the idea of fashion as language, where we communicate part of ourselves through what we wear, as much as I never want to touch a colored polo again. 

So when my little rectangular box popped up on the screen, perhaps I was not only showing off my red and blue teddy bear sweater, but also sending nonverbal messages: I am disciplined enough to dress up even though I have not left my home in weeks. I am cool and environmentally-conscious because I found this at a thrift store in Brooklyn. I need this ritual to preserve my sanity. 

At the end of high school, we each had a journal for our classmates to write parting messages in. I picked a turquoise booklet with a spiraling tree carved into its cover, and wrote my name in all-caps with a sharpie. I let it pass through a series of hands. When I read through the entries, they all had one word in common.

“Your style is so cool.” “Stay cool.” “You are a super cool human.”

One offered the reasoning behind his statement:

“You are a cool person. I don’t mean that in the generic sense. I think you are cool because I don’t ever see you trying hard to impress people or to be what you think you should be. You just are.”

I couldn’t tell why I felt dissatisfied with the compliment. Cool was aspirational, a trait that I ascribed to movie stars and kids in older grades. Serena van Der Woodsen was cool. Brandy girls were cool. But when it was pointed back at me, it felt empty.

Jason Jules, creative director and author of Black Ivy: A Revolt in Style thinks “cool” is something to be avoided. “I’m often called cool, and it feels like a way of limiting my thinking or my intentionality. Like a Black athlete having natural talent, as if it's something that he hasn’t had to work and make sacrifices for. It’s like, he’s just an amazing athlete. You’re just innately cool, you’re born cool.”

For Jules, self-control, awareness, and the determination to shape parts of yourself in a dynamic, unpredictable world underlie what it means to be “cool.” Coolness is not innate. It is made from a series of choices. 

His argument is almost comically in opposition with the sweet note from my friend. But I agree with Jules—I do try hard! I learned how to do makeup by watching YouTube tutorials and practicing on my face before my evening showers. I envision outfits in my head before I try them on, I make a lot of lists, I think too much before I speak.

Me in 9th grade, wearing a Brandy Melville tube top.

I have a hypothesis that if a quiet person dresses relatively well, they will be called cool, and that’s why I received all of those messages. Cool leaves something to be discovered, allowing people to imagine the parts of yourself you are reluctant to share. I was once called “mysterious” by three people in one week. My friends who know me well laughed when I told them, because I am not mysterious at all.

Cool is temporary—what is cool one day may die out the next—and it is frustrating in its opacity. You cannot tease apart the word into comprehensible, tangible pieces, in the same way that you can understand glamorous (pearls, silk, heels) or edgy (black tights, ripped denim). Cool is not so much a style as it is an amorphous, know-it-when-you-see-it feeling that transcends fashion and touches every surface of a person’s identity. Serena’s existence is effortless because she is not an actual person, and being cool in real life requires perpetual intention.

And after all this, I still don’t know how I would define it.

Maybe: Aesthetic self-consciousness. Careful deviation. Mutability.

I also asked my friends for their thoughts.

My brother texted me back after I made the collage.

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See you next week! I would love to hear your thoughts. <3