Despite having “Trouble” tattooed across his neck, the only kind of mischief Trevor Andrew cops to these days is of the parking variety. “I just had to get my truck out of impound,” says the 27-year-old while scanning the racks at the SoHo Burton store on an early February afternoon. “So let me know if I’m dripping sweat, because I was freaking out.”

Inappropriately dressed for the bitter cold in a denim jacket, hoodie and skinny black jeans — accessorized with gold chains, a Gucci belt and oversize pink Oakley sunglasses — Andrew has a scrappy hipster-meets-B-boy look that doesn’t mesh with his “Trouble Andrew” moniker. Nevertheless, he insists, “I’m trouble — in a good way.”

This story first appeared in the February 26, 2009 issue of WWD. Subscribe Today.

A two-time Olympic snowboarder, Andrew is shopping for a few pieces to add to his wardrobe, which, he says, has been stretched thin by the spate of press obligations surrounding the release of his self-titled debut album earlier this month. Fortunately, he is sponsored by Burton and designs apparel for Analog Clothing, the subbrand he helped launch in 2003. Holding up one of his jackets — a black nylon shell emblazoned with photo-realistic images of chintzy gold jewelry, much of it plucked from Andrew’s personal stash, “These graphics were inspired by Canal Street and [Brooklyn’s] Fulton Mall.” What about the door-knocker earrings near the collar? “Those are Santi’s.”

Santi would be his fiancée, Santi White, the indie music and style darling better known as Santigold, who made the rounds last week at shows like Matthew Williamson and Tory Burch. White, as it turns out, was the one who encouraged Andrew to start making music after a knee injury took him off the snowboarding circuit in 2004. She also hooked him up with producer John Hill (co-executive producer of her 2008 record “Santogold”) and lent vocals to the track “Bang Bang” on Andrew’s album, a mix of skate punk, hip-hop, rock and electro-pop.

She’s also offered her beau some fashion advice. “We’re always, in every way, putting each other up on some new stuff,” Andrew explains while trying on a black oversize sweater at his next stop, and one of White’s favorite stores, Seven New York on Mercer Street. “I’m so into vintage stuff for the most part, and making my own stuff,” he says, showing off the handiwork on his jacket: Gucci-print elbow patches, skater buttons, studs and other embellishments that he affixed himself.

Still empty handed, Andrew makes a final stop at high-end vintage mecca What Comes Around Goes Around, where Shaun White, the Olympic gold medalist — and fellow shred-bunny-cum-designer — also happens to be shopping. (He’s in town for the Red Bull Snowscrapers competition and its $100,000 prize, though he doesn’t end up placing in the top three.) “This store is rad,” says Andrew, exchanging a bro shake-hug with White before heading straight to the back of the store. A self-proclaimed eBay addict, Andrew begins digging through a stack of faded T-shirts, but is visibly discouraged by the $300-odd prices for the skate and surf shirts he likely owned as a kid. But then trouble, as it were, finds Andrew: a black motorcycle jacket with star studs priced at $1,500. It fits his slight frame perfectly. “This is dope,” he says to his reflection.

But $1,500 dope?

“I’ll go and make my own. I just got to find a cheap leather jacket,” he says, sliding it off.

A salesperson moves in. “There’s some flexibility on that price,” he says, offering a 20 percent discount on the jacket and a denim vest Andrew also tried on.

In a flash, Andrew’s AmEx is out. Total trouble? $1,584.83.

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