11. Blood Orange Denim Jacket and Matching Hat

Episode: 62 

The Fresh Prince was all about matching his hats and shirts (please don't try this now) and it turned out to be part of what defined his style. Through all the seasons there might not be a doper look than his blood orange denim jacket with the matching snapback. Okay, on second thought try this if you want, dudes are out in the streets wearing skirts.