4. Juicy J
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 togetherâ€”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.