Year Arrested: 2001

Crime: Driving while impaired.

Not only does Federov look fresh in this photo, but he might consider using this 2001 mugshot as one of his modeling headshots. The turtleneck is a piece we expect to see return to prominence very soon, and it looks like Federov was already  ahead of the curve by shearing off the neck, leaving an unfinished hem that's very DIY chic.