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BILLY COTTON’S first apartment, in Manhattan’s Chelsea neighborhood, was a collage of all the things he loved: a wooden bakery cart; a Joe Colombo lamp in egg-yolk-yellow plastic from his grandparents’ house in Boston; and a closetful of outfits for clubbing (“Commes des Garçons mashed up with remnants of my preppy past,” he says with a faint smile). It was 1999, and the Vermont native, 18, had bought the one-bedroom sight unseen before moving to the city to attend Hunter College. He buried its imperfections under a pile of gimcracks. “It was like Miss Havisham’s place—you couldn’t walk around,” he says. “It was my…