HOW MUCH: Buy it now, $65
WHY: Back before indie culture was mainstream, there was always that one kid in school who wore batshit crazy stuff with an air of indifference. The kid who could make anything cool. A bowtie. A jodhpur. Mardi Gras beads. A black Army Navy surplus bag with The Smiths scrawled on it in silver paint pen (oh, sorry, that last one was me). Anyway, this shirt was his -- that guy who said Jules et Jim was his favorite movie in tenth grade, who painted his passed-down jalopy matte black, who wore his hair long over one eye and the tops of his combat boots flopped over purely by accident. It was purchased at the Benetton on Broadway near Astor Place in 1987 when Aca Joe was across the street and the Gap too. Unique and Antique Boutique were just a stroll away. He bought a vintage blazer that day too; three button, stiff three-season wool with a musty smell and subtle blue stripe on grey, a little further down Broadway at Canal Jean. He wears this Silky Rayon Casual shirt, with its candy pots and flowers (he knows what Ambrosoli is because he went to Italy over the summer with his parents) to school on Monday and the lacrosse players call him a fag in the hall outside the gym. With a raise of one eyebrow he adjusts his Walkman, turns up PiL and flips them the bird. Outside to smoke a cigarette on school grounds like it aint no thang.