15. O.J. Simpson
Year Arrested: 1994
One of the most iconic images of the '90s was O.J. leading the LAPD on a slow-speed chase in his vintage Ford Bronco as he tried to evade being arrested for the murder of his wife Nicole Simpson. Once he was finally nabbed, his mugshot was snapped while wearing a yellow polo under a navy blazer - classic weekend wear for the rich and famous.