André 3000

André 3000 spent the Outkast years mixing argyle, kilts, platinum wigs, jodhpurs and golf caps at award shows, most memorably across the 2004 Grammys, where Outkast won album of the year. He treated preppy and country-club menswear as raw material for something theatrical, and his later choice of a jumpsuit and a flute on red carpets kept that independence going.