If it weren't for his proclivity to sleep with women, guys like hockey player Sean Avery might go by the label "gay." Yep, the man loves clothes, and we love stereotypes. Though he's "the most hated man in hockey," he was likable enough for Anna Wintour, who agreed to hire him as a Vogue intern after he wrote in with the request. Though he's earning $2 million with the New York Rangers, this summer he'll be schlepping couture from messengers to the Vogue offices, perhaps even the Men's Vogue offices, though that won't do much for his tendency to style girlfriends.