Love her or hate her, Anna Wintour has the ability to make and/or break careers in the fashion world and beyond. Every couple of seasons she seems to take a shining to certain athletes, increasing their overall exposure in the fashion world and introducing them to an entirely new portion of the public. In the past she has been seen at shows with Amare Stoudemire, Serena Williams, and Roger Federer. So, in anticipation of Fashion Week, what better way to combine the worlds of sport and fashion than by placing odds on who Anna will pick as her next front row companion? More»

Watch out, Roddick and Blake! This NYC Socialite is on the prowl. Who is it? Hint: She loves to run down Fifth Avenue during rush hour. Find out who below... More»