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The 50 Biggest Athlete Style Fails

45. Sean Avery is photographed in Terry Richardson's sex-dungeon.

When: 2012

Sean Avery made sure that everyone knew he was into fashion when he was still on the NY Rangers. Well in case you forgot, here's Avery in all his glory being captured by the famed Terry Richardson, who somehow manages to get every single photo subject out of at least half their outfit, Avery included. While it's unknown for sure if Avery has retired, who would dare to go back to the NHL after this photoshoot? He'd be skating all day with a target on his back.

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