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Michael Phelps

Michael Phelps sat front row with Anna at Jeffrey Chow's Spring 2005 show (naturally, he dressed casually for the occasion). Though Michael hasn't landed a Vogue cover yet, he was featured in the April 2008 issue.

Image Source: Getty
Read More Michael PhelpsAnna WintourKate BosworthKate MossSarah Jessica ParkerFashion WeekCelebrity StyleBradley Cooper