Confessions of a Recovering Hypebeast

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First day of college and I'm woefully unprepared for life at NYU. I went to Catholic school. I've worn a uniform for the better part of my life. And now I'm walking around the most fashionable city in the world, dressed in jeans that are ten times too big for me and a printed tee that lets the world know two things: I still play Sonic the Hedgehog video games, and I have no idea how a shirt is supposed to fit.

At the private schools where I went as a kid, uniforms and homogeneity were staples. From kindergarten through eighth grade, I wore green pants and a white button-down, while my Jesuit all-boys prep school was a consistent blazer-and-tie affair. My wardrobe was set for about 80% of my life, and for the other 20% I made do with a poorly thrown-together combination of baggy hand-me-downs, Timberlands, and graphic tees I got from Hot Topic. Did I mention how socially awkward I was? The all-boys-school upbringing did not help.

It’s not hard, then, to imagine my shock and wonderment upon moving to New York City. From the moment I first left my dorm in Union Square, I was surrounded by people, all them blessed with their own sense of style and identity. It showed in what they wore, how they looked, how they carried themselves. And there I was, dressed like a mess—which was also how I felt.

One morning, sitting in the park before a liberal arts class I could never stay awake for, I noticed something in my downward gaze. Sneakers. But not just any sneakers. They had the trademark Nike swoosh on them, and the underlay and vamp were plain white. But the tip, collar, and eyestay had a print on it that I had never seen—like cracked pavement. I had never seen a shoe like that before. Where could I find it? How could I get? I had to know more.

I looked up to take in the rest of the guy's outfit: Pristine raw denim with a smiley face on the butt. A rainbow-colored hoodie that looked like it was made of cotton candy. Around him were other guys all dressed similarly, wearing what I would later learn to be a combination of Nike SBs, BAPE denim, Billionaire Boys Club hoodies, and Supreme Hats. They stood out. They weren't just bland faces in the crowd; you noticed them. I didn't know where to start, but I wanted to wear that stuff.

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Fast forward six months. It's cold out. It's also really early, maybe 5am. I don't normally like waking up at this hour, but it's what needs to happen if you want to cop new releases. And so here I am, waiting in line at the Soho Branch of BAPE with my cousin in the wee hours of the morning.

Hours go by. Numerous Red Bulls are consumed. Some eager new faces got there ahead of us, so we're not first in line—the price we pay for slacking off a bit after many previous successes. There's a limited number of $350 hoodies available, 100 to 150 at most. Luckily, this time I won't have to borrow some money to meet the price tag.

After three hours of waiting we finally get in. The streak continues! There hasn't been a new release yet that we've missed out on. Of course, there are only a few hoodies left, and my size is sold out, but I'm happy to settle for a large. "Hey, it's only two sizes too big for me," I tell my cousin, feeling triumphant.

Pharrell, Swizz Beats, and Nigo, 2007. Photo: Getty.

I would never have used this term, but I'd turned into what some people would call a "hypebeast." Urban Dictionary, that repository of Internet truth, defines a "hypebeast" as "A kid that collects clothing, shoes, and accessories for the sole purpose of impressing others. Although the individual may not have a dime to their name they like to front like they are making far more than everybody else."

Even before sneaker culture really exploded in the mid-2000s, propelled by celebrities like Kanye West and Pharrell, "hypebeast" carried a negative connotation. We wanted to seem like "OGs" or "Original Gangstas"—people who had been collecting shoes and clothes since the infancy of streetwear culture, which can be linked back to the rise of hip hop and the first-ever pair of Air Jordans in 1985. With basketball and hip hop both gaining popularity, the sneakers and the clothes associated with them became status symbols. By the time I was waiting in sneaker lines, in the mid-aughts, streetwear fandom had expanded beyond just the small group of hip hop and basketball fans into a bona fide subculture that everyone from suburbanites to celebrities wanted to join.

For me, it started off with a couple pairs of Nike SBs and some BAPE sneakers. Whatever my paltry part-time salary would allow. Then I upgraded to Kid Robot and 10 Deep hoodies, rounded out with shirts from Stussy. By the time I was a senior in college, I had amassed a giant collection of shoes, hoodies, jeans, and shirts that was worth (on paper) well more than what any college student should be spending on clothes.

Every spare penny I made went into my wardrobe. Every extra moment I had went into trolling sneaker websites trying to get the most up-to-date information on new releases and the best times to grab them. And I was proud of the fruits of my labor. Some of my most prized sneakers, also referred to as "Holy Grails," included Supreme Lows, De La Souls, and Tiffanys. Those three alone nowadays could pay for the rent on a Lower East Side apartment for two or three months. I've worn them a combined total of three times, ever.

I wanted clothing that spoke loudly on its own because I was too awkward to speak up myself. And amazingly, it worked. Soon after I started wearing "hypebeasty" styles, people my age looked at me differently. They noticed me, which is something that never happened to me.

I was becoming a regular at downtown stores like BAPE, Kid Robot, and Reed Space. Other shoppers would talk to me and ask me my opinion about things, like I was some kind of authority. Me, the awkward kid who'd barely had a normal social interaction with anyone until I got to college! After decades of blending in, I was finally starting to stick out.

By this point, I had a constantly-updated shopping list in my brain, and I would do anything to ensure that I always copped a new release. I camped outside stores more times than I care to admit. I ate cheap deli food and dollar slices to offset my spending, if I even ate at all. The most egregious incident was probably the time I paid an employee of a store to sneak us a hoodie—for the full price of a hoodie. If you're doing the math, that's somewhere in the vicinity of $400 on top of an already $400 hoodie. But I knew what I wanted. And I knew I had to have it.

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First day of work. First job, first actual salary. I want to show up at the office looking smart and professional, like hiring me was the best move they'd ever made. I look into my closet: Nothing. There is literally not a piece of clothing in my closet that I can wear into an office without looking like a hiring manager's worst decision. Time to panic.

Something changes once you start a job in a professional setting. People aren't looking to your clothes to do the talking any more. They want you to come up with ideas, solutions to problems, your point of view on big things, none of which can be communicated by your $400 sneakers. All around me, the guys I'd waited in line with for new releases were trading in their expensive kicks for clean dress shoes, their hoodies for sharp blazers, and their raw denim for a comfortable pair of office pants. Now, we were sitting on tens of thousands of dollars of clothing with no time to wear it, and no one to notice or care for it.

Over the course of the next year, my hypebeast gear started to draw cobwebs. I became more concerned with comfort and ease, and I was more concerned with letting my actual words speak for me, and not have my clothing be a distraction. Slowly but surely, I began to sell off a lot of what could be sold. Sneakers went first, and a couple hoodies. The shirts, though, were unsellable, and many of the more over-the-top hoodies went unbought. Now my mom wears them around the house. She says she likes them because they're warm and comfy, and make her feel like a cartoon character.

Whenever I mention my hypebeast past, the question I'm always asked is "Was it worth it?" When this happens, I pause. And I think about all the time spent on lines in front of stores in the chilling cold. I think about all the money that could have eventually gone to paying back my enormous college debt. I think about all the friends I made talking over sneakers and clothes, however short or long those friendships may have lasted. I think about how I finally felt like a person with an identity, how I finally stopped worrying about being socially weird. And I'll reply, "I think so?"