20. Silk Shirt, Black Jeans, and Nike Huarache Runners
When you have that Bel-Air financial backing it's easy to diversify the closet. Silk shirts and black denim were the rage in 1992 and Will always had to stay laced in the illest sneakers our, Huarache Runners easily suffice. Most people might be more familiar with the Huarache Trainers but after Will let Philip Bank's arch-nemesis, Jazz, crash at the crib we are pretty sure he scooped a pair of runners to get away from Uncle Phil the easiest way possible — actually moving at a moderate pace. Always scheming Will, we see you.