Juicy J has his ups-and-downs. The Three 6 Mafia member has enjoyed a prolonged career, and is even more popular now as a solo artist than when he was asking his listeners to "Tear Da Club Up." He was also featured on a Supreme T-shirt as part of the brand's fall/winter 2012 collection, and yet, he still struggles with looking fresh on a regular basis.

The Memphis rapper has access to a lot of good clothes, and often has the right idea when putting an outfit together—but fails to connect all the pieces. We've seen him wear cool streetwear ensembles, but he ends up looking as comical as his rhymes. He also rocks a fedora on the reg, not knowing it's the worst hat ever.