5. Michael Irvin
Michael Irvin, who won three super bowl titles in the '90s alongside Emmitt Smith and Troy Aikman, is no stranger to controversy over his fashion choices. When he made a court appearance in 1996, Irvin made headlines by showing up in a full-length mink coat. Currently an analyst for the NFL Network, the self-nicknamed "The Playmaker" needs to find a jacket maker. Michael Irvin looks like the cheesiest mobster of all time, and now that he's clean the cocaine cannot be blamed.