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For athletic style inspiration, there’s nothing quite like a late-summer rewatch of the most iconic tennis matches. From legend Billie Jean King’s early years to today’s Wimbledon matches, the ensembles on display balance court-ready practicality with subtle nods to timely trends.
We scoured the archives for the most head-turning, easy-to-copy outfits from the past five decades. You’ll notice quite a few from Venus and Serena Williams, considered some of the most powerful players (and likewise, best dressers) on the court, plus more recent icons like Coco Gauff and Naomi Osaka. Ahead, we’re walking through 23 of the most iconic tennis looks of all time, highlighting our favorite athletes’ most boundary-pushing style.
