Tennis is a sport of style. From the elegance of a baseline player whipping long ground strokes over the net to the agile cunning of the serve-and-volley game, styles of play win matches. Styles of dress, however, win hearts. Björn Borg's iconic outfits endure, and the Williams sisters' beaded braids are almost as memorable as their winning legacies. And it isn't just the pros—Wes Anderson and Woody Allen have channeled the preppy cool of tennis style in film, and legendary beauties Katharine Hepburn and Farrah Fawcett had game in real life. To celebrate the beginning of the U.S. Open, here's a look back at the greatest tennis fashion moments of all time, from the court, the screen, and the runway.