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.

Rough and tough is how we raise our boys, but make sure they're ready to face the storm in style with the right jackets and vests. Kids' lines from Diesel and Ugg make ultra-durable and super-stylish military-inspired coats and vests for growing soldiers. Athletic lines like Adidas let him channel his favorite sports hero.

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.