The Rapper: Mos Def
The Women's Clothing He Wore: Earlier this year, an image of Mos wearing a multicolored "wrap" in South Africa surfaced on Twitter and many people assumed that it was some kind of skirt.
How Ridiculous Did It Look? Initially, pretty ridiculous. It became slightly less ridiculous when Mos explained exactly what he was wearing. But we still never imagined that we would see him wearing this outfit when he first debuted back in the late 1990s.
Photo Credit: Obnoxious TV