Cindy Crawford’s Challengers tennis fashion tour has so far come with heaps of custom court-inspired outfits, from a to an ethereal. Over the weekend at a Milan photocall, Zendaya and stylist decided to flip their bespoke-only script, dipping into Ralph Lauren’s archives and borrow a look last seen on legendary model.
Z appeared on the Challengers step-and-repeat in a short, fitted tennis dress with a polo collar and a flouncy, full skirt. She paired it with her two most frequent accessories on the tour thus far: white Louboutin heels and Bulgari jewelry.
Zendaya’s Challengers Milan photocall dress was first seen on Ralph Lauren’s Spring 1992 runway.
Her country club-appropriate look turned out to be another incredible archival pull. Roach sourced the piece from Ralph Lauren’s Spring 1992 collection, where it was first modeled more than 30 years ago by Cindy Crawford.
The vintage piece didn’t appear to have modifications or extra accessories compared to its runway debut. In both the past and present, it was styled minimally to let the fitted bodice and full skirt do all the work.
Cindy Crawford first modeled the dress that Zendaya would wear to promote Challengers more than 30 years later.
Zendaya being Zendaya, borrowing a look from Cindy Crawford was just one of four major outfits she wore for another weekend of hard-hitting Challengers promo. For a Saturday spent courtside at the Monte Carlo ATP Masters Series Tournament in Monaco, Zendaya first appeared in a cable knit sweater and longline skirt by Brunello Cucinelli.
She changed into another outfit rich with fashion history after a quick photo op. Her second look entailed a custom polo tank top tucked into a pleated skirt by the athletic brand On. The pieces, Law Roach shared on Instagram, were inspired by the tennis whites worn by Althea Gibson—the first African American tennis player to win a Grand Slam, in 1956.
For a Saturday appearance at the Monte Carlo Masters, Zendaya wore a slouchy cable knit sweater and slit skirt from Brunello Cucinelli’s Fall 2024 collection.
After her Brunello moment, Zendaya changed into a custom On set inspired by Althea Gibson’s tennis whites.
Following her stops in Monaco and her red carpet in Milan, Zendaya had one more twist on tennis whites up her sleeves. For a visit to the Italian talkshow Che Tempo Che Fa, the 27-year-old changed into a custom terrycloth mini dress by British label 16Arlington. A trusty pair of Louboutin heels completed her all-white look once again.
Rounding out her weekend in white, Zendaya appeared on the Italian talk show Che Tempo Che Fa in a white 16Arlington mini dress with a scoop neckline and gathered bubble skirt.
Zendaya’s days of acing Grand Slam-inspired fashion are coming to a close soon. The final stop on her tour appears to be a Challengers Los Angeles premiere on Tuesday, April 16. All the pleated skirts, polo collars, and tennis whites she’s worn leading up to this moment are having an impact on style IRL: Instagram account reports that searches for “tennis fashion” are up 80 percent this month.