His first words to me were “Nice jacket,” an opening line that was bound to stop a girl like me (fashion obsessive, proud collector of vintage outerwear) in her tracks—or at least, it should have. In truth I was way too shy to acknowledge Tyrone (pro skater, incorrigible flirt), my first love’s advances in the beginning, and I shuffled past him in my forest green field jacket, eyes cast down, trying not to turn beet red. It wasn’t until our paths crossed the second time, when he followed me home on his board like a lost puppy dog one day after an art opening in Bed-Stuy, that I even realized he was a skater boy. Growing up in London, I had fallen prey to my fair share of flamboyant douchebags—soccer stud, club promoter, wannabe rock star—but skater boy lust wasn’t something I knew, and yet it hit me like an ollie gone wrong on the sidewalk—hard and fast.
He was cute and he knew it. The cheeky grin, the scruffy Afro, the dirtbag zero-fucks-given attitude all worked in his favor, but it was his unstudied sense of cool that really had me hooked. His Nikes were always scuffed just so; his flannel shirts had a rumpled, partied-all-night swagger about them; he cinched his baggy jeans around his gangly frame with shoelace strings, a styling trick that was as punk in spirit as he was. It wasn’t long before I was sleeping in his Supreme T-shirts, claiming his free skater swag as my own—beanies, hoodies, you name it. Finally I’d met a guy who got my rough-and-tumble tomboy looks—the oversize coveralls, the vintage bowling shirts, the retro Adidas tracksuits—a guy who didn’t subscribe to the notion of sexy as some trussed-up, spandexed idea. And though he wasn’t exactly wooing me with red roses and trays of chocolates every night, his romantic gestures had a certain stylish flair: He’d leave scraps of paper scribbled with sweet nothings in my dresser, and would graffiti my agenda with graphic I-Luv-Us.
If I’m totally honest, the pro skater thing wasn’t always a plus; as cool as his novelty socks were, the stench of them after a long day of skating was enough to wake the dead, and his idea of date night was sneaking into an abandoned building with takeout burgers from White Castle and a six-pack of beer. Reliability was also not his strong suit; though he promised to pick up my mother from the airport on her first trip to the States, he was nowhere to be found when her plane touched down at JFK. We did eventually find him wandering the parking lot with a broken deck for a sign, scrawled with the words “Welcome to America, Chioma’s mom!” Of course, he had us both wrapped around his little finger by the time we got home, laughing our asses off. “Tyrone is like a glass of champagne—fun for the night, but you’ll always wake up with a hangover in the morning,” was my mother’s summation. She wasn’t wrong. As thrilling and exciting as he was, the bubbles burst on our relationship pretty abruptly when I found out that he had a live-in girlfriend, out in L.A., where his team was based. I was crushed.
Thirteen years and several boyfriends later, and I still have a soft spot for that skater boy thing, and I’m clearly not the only woman working in fashion who does: Phoebe Philo made slip-on skate shoes a staple part of her sophisticated Céline wardrobe, Jayne Min was a skateboard apparel designer before she was a street style star, and I’ve literally lost count of the number of times the Thrasher tee—holy grail of skater style—has been appropriated by models off duty. “I still get goose bumps when I hear the sound of skate wheels turning,” a fashion PR friend in her mid-30s confessed to me recently. “People told me I would grow out of it, but I never did.” I was reminded of that uncanny skater-boy-fashion-girl symbiosis again, when a downtown restaurateur acquaintance of mine revealed the marketing strategy for his new café: “We know if we can get the skaters in here, the cute fashion girls will follow.” Ladies and gentlemen, go figure.
Looking back on the heartache and the drama, would I do my skater love affair over? Maybe, maybe not. The good news is I don’t have to date one to get his clothes—there are plenty more options for those of us with a crush on skater style these days, as Vogue.com Market Editor Chelsea Zalopany proves with cool Margiela playsuits and super wide-leg SJYP jeans. Does that mean I’m ready to throw out Tyrone’s hole-ridden skater boy hand-me-downs? Probably never.
