5. Andre 3000
Height of Style: "Hey Ya" video
Signature Look: Throw-back dapper gentleman.
After being the first rapper to get Erykah Badu’d in the late '90s, Three Stacks reconfigured a Funkadelic style that drew heavily on George Clinton, Bootsy Collins and Bambaataa. He went on to father to Janelle Monae’s style and the man behind the retro-preppy Benjamin Bixby clothing line. Ever the contrarian, Dre has experimented with turbans, blond wigs, shoulder pads, a modernist take on Nat King Cole, and barbershop quartets. In recent times, he's settled into the more gentlemanly figure featured in those razor commercials.