Vintage D.A.R.E. shirt from No Relation Vintage in New York City

Let’s hit the racks,” Kid Cudi announces as he strolls down 11th Street in New York City. The rap wunderkind is rocking denim cutoff shorts tethered to his slight frame by a brown leather Louis Vuitton belt with an oversized gold monogram buckle; a white T-shirt that he sniffs to check if its expiration date is coming; Air Jordan Infrareds; what can most easily be described as solid gold Mardi Gras beads; and, of course, his thick-rimmed glasses, which, in another life, could have rested on the bridge of the nose of a shag carpet salesman in the 1970s. He eschews the marbled shopping palaces of Fifth Avenue for the humble coat hangers of vintage shops downtown; with Cudi, everything that is old can be fashion-forward.

The first destination is a dope secondhand store, Buffalo Exchange—the Wild West of the East Village, where the hip fight each other to snatch a treasurable item from someone else’s castoffs. The shop houses everything from beat-up combat boots to preppy polos, leaving patrons to wonder whether their purchase was the jewel of someone’s closet or a freebie T-shirt from a company picnic. Either way, every article is fit for a good home. Before he hits the front door he’s swarmed by a meandering group of young day-campers.

“Are you … you …” one half-brave girl utters, “Kid Cudi?”

With a smirk he returns, “Yeah, I’m Cudi.”

Despite the heat from the most oppressive summer the city’s had in recent years and the teeming midget mass descending on the A-lister, Cudi keeps his cool and wraps his arms around the group, waiting patiently while the campers fuss over who will take the picture. He plays arbiter, suggesting that they all get a chance to take turns as cell phone photographer, then hangs tight as not-yet-fully-formed fingers fumble on the shutter button. Damn the possibility that some other guy may be in Buffalo Exchange plucking the perfect threads earmarked for him, Cudi takes the time to connect with each kid. While most of an average person’s life diversions are electronic, coming in the form of e-mail or Facebook update, his are immediately personal, and he handles them with grace and aplomb.

Cudi takes his cool into the thrift store. Other shoppers rip through the racks treating unsatisfactory clothes like spam e-mail, while Cudi stops to consider each item, calculating how it fits into his opus. He contemplates certain shirts, sometimes going back to them again and again, in the same vein he might while contemplating a beat or rhyme for his next song. His approach is nothing if it isn’t free-form poetic.

“I don’t go out looking for anything in particular when I shop,” he says. “I try not to think too much. It’s about the feel, comfort.”

He blesses a tee with writing that screams “Bad” by slinging it over his shoulder. Conceivably it pays homage to Michael Jackson’s prime, as the once-bold red has faded to a pale pink, only further accentuating how bad/awesome it is. He hops into a dressing room and swaps his white tee for the shirt pressed before the school kids outside were zygotes. “This is bad,” he says, showing off his first catch.

He gets back to the madness on the shop floor and hooks a black T-shirt with white writing on his second cast.