Earlier this year, Serena Williams and Roger Federer stole the spotlight when they won the Australian Open in their mid-30s. They wowed again a few months later, this time at the Met Gala in New York City, with Federer donning a Gucci tuxedo with a crystal snake design, and Williams proudly toting a baby bump.
It was hardly the first time either superstar has made waves off the court. Federer’s friendship with Vogue editor in chief Anna Wintour is well documented (the fashion maven has also been linked to Caroline Wozniacki and Grigor Dimitrov), while Williams—when she wasn’t filming a music video with her pal
Beyoncé—went on to grace the pages of the Sports Illustrated Swimsuit Issue with Wozniacki and Eugenie Bouchard. In June, a pregnant Williams was on the cover of Vanity Fair.
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