High school was all about casting about wildly for the activities that would define you, like crew, and furtive masturbation. For gear that facilitates a fluid identity, check out Public School, just now in stores.
From two former Sean John-ers/NY public schoolers, PS's dark-hued, truant-inspired gear allows you to modify your appearance on a whim -- like that Wildenstein Cat Lady, except people won't claw out their eyes as you walk by. The permutability starts w/ the nattily thuggish outerwear: leather bombers from which you can detach the epaulets, cinched short-waisted jackets whose collars flip between spread and mandarin, and black leather biker vests whose fleece hood and sleeves you can zip off -- like breakaway pants for men too prude to risk a game of peek-a-balls. The shirt and hoodies are flexible too, from polos w/ special high-cut collars (sturdier poppage), to a black hoodie with waist-high, Mr. Rogers-esque front pockets -- stow the hood, and break yo' self, neighbor.
PS'll also garb you in graphic tees and jeans, solid pieces that nonetheless force a single, consistent personality, i.e., the well-dressed coxswain who's always urging others to "stroke".