16. Denim Button-Up Shirt, Jeans, and Nike Air Force High
The two-toned denim on denim look is always dope if executed and Will killed it with one of his more conventional looks. No sneaker made as many appearances throughout The Fresh Prince of Bel-Air than the classic Nike Air Force High — it wasn't even close. They saw his first apartment (which he was kicked out of within 24 hours), Carlton losing his virginity, and Will meeting his biological father.