As both a fashion editor and tennis player, nothing brings me more joy than commenting on tennis outfits. Serena Williams is not only the GOAT because of her on-court skills, but also her fun, daring, and inventive tennis outfits. If there was any doubt about her fashion relevance, she broke the news of her retirement on the oh-so-coveted cover of the September issue of Vogue. 

“I’m torn: I don’t want it to be over, but at the same time I’m ready for what’s next,” Serena wrote in a letter published in Vogue. “I don’t know how I’m going to be able to look at this magazine when it comes out, knowing that this is it, the end of a story that started in Compton, California, with a little Black girl who just wanted to play tennis.” To honor the Greatest of All Time, I’ve rounded up some of her most iconic and controversial outfits of all time.