Anna Wintour is the biggest name in the fashion biz. Translation: She can pick and choose her BFFs. You might think she'd select a designer, a supermodel or a movie star, but you'd be wrong. She fancied a famous tennis player. Well, not just any player, but arguably the greatest tennis player to ever grace a Grand Slam court. Did we mention that he's a dapper dude with one of the classiest off-court demeanors? Nicely played, Ms. Vogue.