10. Flannel, Jeans, and Nike Air Maestros 

Episode: 87 

The best part about Will Smith's style was he had the courage to do things most people couldn't wear outside of a music video. He also killed it in toned-down outfits that every kid could appreciate. In episode 87 he paired up a flannel and jeans—nothing too wild or over the top, but definitely one of Will's best outfits on the show. Sometimes less is definitely more.