“Never, never, never hold it like that!” Professional skateboarder Brian Anderson is leaping across a gravel-strewn lot at Coleman Playground to correct my grip on a borrowed skateboard: Wheels are to face in, not out, hold by the board, not the “truck.” And if you want to be cool, not the bottom of the deck facing out, even though that’s where the stickers are: “That’s the mall grip.” Now, I may not know much about skateboarding, but I know enough to know that being described as a “mall” anything is seriously less than ideal. I switch the board, scrunch a sleeve to show a flash of Crayola-color Swatch, lean back like my legs are sore from ollieing all day and try to blend in. I catch a flash of side-eye from a twelve-year-old boy. We’re wearing the same hat. It’s very “Who Wore It Better: LES Youth Edition,” and I’m pretty sure I’m losing. This, suffice it to say, is not my normal Wednesday.
It all began a week ago in the Vogue offices, when my editor asked whether I might consider getting a skater makeover in honor of Odd Future’s insanely cool and largely underground skate premiere for Illegal Civilization. “Ice skater?” I asked hopefully, picturing layers of abbreviated tulle, waist-cinching leotards, illusion-net necklines, a “Good Swan On Ice” thing. Yeah, I could do that. “Nooo,” she said, “skater-skater. Baggy pants and skateboards. Styled by a pro!” Being in possession of both eyes and working synapses, I am very aware of fashion’s current vogue for skate culture—look no further than the recent collections and advertising campaigns of Hedi Slimane, Marc Jacobs, and Phoebe Philo, those venerable tastemakers—which is not even to mention Supreme, with its SoHo-disrupting all-night queues and perpetually wait-listed graphic tees, or the bevy of sylphs (Daria Werbowy, Cara Delevingne, Hanneli Mustaparta) who glide on their boards to and from the shows. Like so many things, I enjoy the look! On other people.
For one thing, I think it’s important to know one’s limitations, and I don’t think I’m selling myself short to say I am not great on wheels. (I’ve got the battle scars to prove it; stitches from various early expeditions on bicycles, road rash from a Vespa, etc.) Sartorially, too, I am not really of the skatepark school: I traditionally favor slim-cut pants, for one thing. I have already aired my feelings about flattering footwear, and just the other day I used “skater punk” in a negative sense. But I am nothing if not up for a challenge.
The skater dress sense is not so easily explained, it turns out. At our first meeting, Anderson, a one-time Thrasher magazine Skater of the Year with his own company, 3D Skateboard Co., and over a decade-long relationship with Nike (for whom he designed the Nike Project BA skate shoe, among others), is wearing a Marc Jacobs waxed jacket he painted the back of “a few years ago” that’s easily the coolest thing I’ve ever seen.
“I’ve been dyeing my hair and cutting up all my clothes like crazy since forever,” he says, so this shoot doesn’t feel like much of a stretch. We begin a list of what I’ll need to blend in with him at the skate park, and when the talk turns to sneakers, he casually points out two men in a Lower East Side coffee shop who are wearing Nikes designed by his compatriot, Stefan Janoski. I nod in what I hope looks like knowledgeable fashion and tuck my Tod’s driving moccasins further under my chair. “Layers are good,” he says, producing a brown paper bag on which he’s scrawled several looping Sharpie designs, making a note to bring some of his more popular shirts. His cuff betrays an underlying flash of a loved-up cream-colored thermal shirt, the kind you throw on and scuff around downtown in to-do errands, the kind that probably cost nothing and somehow always looks amazing. I want a cream-colored thermal shirt! “Do you have a flannel, maybe? Those work: girls will wear one and tie it around their waist when they get hot.” I decide that I have access to a flannel. It may not technically be “mine,” as much as my boyfriend’s, and it may in fact be older than I am, but it will do. “Old is good,” he grins, “I’m going to wash everything you’re wearing tomorrow a few times so it gets that good, lived-in softness.” Jeans? Thank god for that wide-legged story. “These are pretty tight, for me,” he says, gripping a loose fold of his black denim. Sure, I nod, pretending that “tight” in my world doesn’t mean “painted on.” Skate style appears to be about comfort, with an eye-catching bend. You need to stand out from other skaters, and from the tricks themselves. “I’ll bring some flair to make it pop,” Anderson says decisively. “We’ll make it work.” I am not so certain, but I admire his confidence. We part: he is off to source some goods from surrounding skate shops—Labor carries some of his decks as well as his line of flamingo-and-cyan-colored socks—and walk his Yorkie, Lloyd. I go home to stare at my seriously uncool clothes.
The day of the shoot: I arrive at the skate park. I did not know this place existed, and neither did my cab driver, who joins me in watching the urbane youths making gravity-defying tucks and twists and sometimes just skating back and forth, sometimes just watching each other from the sidelines. I find Anderson, and we duck into an adjacent lot, where he holds his coat over me (“I have eleven sisters,” he says sweetly) while I change into the look he’s styled. A group of teenagers has gathered to ask Anderson to take photos with them, one holds an early deck he designed for Girl skateboards out like an offering. Soon I am dressed: a 3D Skateboard Co. long-sleeved tee, replete with Marc Jacobs–esque Hawaiian flowers cascading down the arms, my trusty borrowed flannel tied around my hips (why don’t I tie more things around my waist like this? What did the nineties impress upon me that I don’t allow myself that?), the slouchiest jeans I own, bright red Nikes, a red watch, and a dog tag that reads “Brian Doe.” I feel surprisingly less like a fraud than I’d imagined. I am also insanely comfortable. “Cool,” Anderson says, heading toward a ramp to do some light spins and grinds and things I don’t know the names of, and I feel awash in his affirmation. “You look totally legit, like we just went skating.” I survey the park: nobody’s staring, nobody’s pointing. My transformation took about five minutes, if you don’t include the fretting, and I look rather cool, if I say so myself. I don’t dare get on the board, but as far as they know, I skated here.
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