12. Design Pocket Tee, Skidz Pants, and Air Jordan Vs
Denim was far from a fail in the 90's but Skidz and Zubaz were the shit. Why wouldn't you want to rock the most comfortable baggy pants that were basically glorified pajamas? In the first season Will paired them with a designer pocket tee shirt which blew up again in 2012 and a pair of "Grape" Jordan Vs set to re-release this spring. Dude really was ahead of his time — having a sick wardrobe budget couldn't have hurt.