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Zendaya’s Challengers press tour moved to Milan yesterday, and the actress wore not one but two white tennis minidresses to promote the project. Throughout her appearances to promote the movie, Zendaya and her stylist, Law Roach, have served one tennis-inspired look after another, sometimes pulling deep into the fashion archives to do so.
Zendaya’s first outfit yesterday, an A-line minidress with a collar and halter neckline, is a striking example of this. The Ralph Lauren piece originally debuted during the house’s fall/winter 1992 ready-to-wear show, worn by supermodel Cindy Crawford. Zendaya wore her hair down, with her shoulder-length blonde locks styled in Marilyn Monroe-like waves—a hairstyle not too far off from Crawford’s runway look.
Cindy Crawford modeling Zendaya’s dress in 1992
Zendaya switched into a second minidress, one with a square neck and ruched skirt by 16Arlington, for her appearance on Italian show Che Tempo Che Fa. Zendaya accessorized the terry cloth piece with Bulgari jewelry, including diamond stud earrings and a pendant necklace. Zendaya is an ambassador for the jewelry brand.
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These were just half of Zendaya’s outfits over the weekend. On Saturday, she wore two other white outfits during her stop in Monte Carlo, Monaco. Zendaya took a break from photo calls and premieres to enjoy a tennis match, attending day 7 of the Rolex Monte-Carlo Masters at Monte-Carlo Country Club.
She had two outfits at the venue. Her first was a knit long-sleeve polo paired with a cream skirt from Brunello Cucinelli’s fall/winter 2024 collection. Zendaya accessorized with Bulgari jewelry, too.
Her second outfit, which she wore to watch the game, has an extraordinary backstory attached to it—one that epitomizes the level of thought Zendaya and Roach have put into every outfit she has worn while promoting Challengers.
As Roach revealed on Instagram, the team at On recreated “the ICONIC tennis white of Althea Gibson” to make Zendaya’s two-piece set. He shared a closer look at the On outfit, along with Gibson’s original look that inspired it.
Gibson was the first Black American tennis player to compete at the U.S. National Championships and Wimbledon in 1950 and 1951, respectively. Zendaya’s stylish tribute is a poignant nod to her legacy.
Althea Gibson in 1950 at the West Side Tennis Club in Forest Hills, New York.