Let him run a muck in preppy polos from Diesel kids and Billabong. He might not want to go shopping, but these t-shirts and polos are guaranteed to get wear and tear if you surprise him with your style savvy ways.
From baggy to bootcut, nothing should come between a boy and his pants--just make sure wears them right. Ample selection of cargos, khakis, and denim from brands like Hurley, Matix, and Volcom, pair easily with his favorite tees and hoodies. Just make sure that wearing the pants doesn't go straight to his head.
Don't just call him a hoodlum; let him sport the Mongoose Zip hoodie from Volcom in true jail-bird fashion. Billabong, Matix and Element out-perform the competition, and keep him incognito oh so stylishly.