5. Mike Tyson
Back in the '90s, you didn't criticize Mike Tyson's style, because then Mike Tyson would kill you. Luckily, Iron Mike was very well-dressed when palling around with his buddies Jean-Claude Van Dame and Tupac Shakur. Before he went to prison on a rape charge in 1992, Tyson was rocking velvet slippers along with rococo pieces from Versace and other designer labels. After he got out in 1995, his boxing career started its prolonged decline, but his style game was still on point for a few more years. Before he became a national joke and the star of the country's collective nightmares, Tyson was ruling the boxing world while draped in very luxurious loungewear.