Zendaya Re-Wears Cindy Crawford's Runway Ralph Lauren Tennis Dress for 'Challengers' Milan Photocall

It was one of four tennis white looks she chose for hard-hitting 'Challengers' promo this weekend.

Zendaya on the Challengers milan photocall carpet in a white tennis dress worn by cindy crawford
(Image credit: Getty Images)

Zendaya's Challengers tennis fashion tour has so far come with heaps of custom court-inspired outfits, from a racket-embellished Thom Browne dress to an ethereal Louis Vuitton gown. Over the weekend at a Milan photocall, Zendaya and stylist Law Roach decided to flip their bespoke-only script, dipping into Ralph Lauren's archives and borrow a look last seen on legendary model Cindy Crawford.

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 at a Challengers Milan photocall wearing a vintage Ralph Lauren tennis dress first worn by Cindy Crawford and a pair of white louboutin pumps

Zendaya's Challengers Milan photocall dress was first seen on Ralph Lauren's Spring 1992 runway.

(Image credit: Getty Images)

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 wears a white low back tennis dress on the Ralph Lauren runway in 1991

Cindy Crawford first modeled the dress that Zendaya would wear to promote Challengers more than 30 years later.

(Image credit: Getty Images)

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.

Zendaya wears a cable knit sweater and long white skirt at a Challengers appearance in Monaco

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.

(Image credit: Getty Images)

Zendaya wears a custom white tennis set from On at a Monaco press event

After her Brunello moment, Zendaya changed into a custom On set inspired by Althea Gibson's tennis whites.

(Image credit: Getty Images)

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.

Zendaya appears on an evening Italian talk show wearing a gathered white mini dress and white heels

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.

(Image credit: Getty Images)

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 @databutmakeitfashion reports that searches for "tennis fashion" are up 80 percent this month.

Halie LeSavage
Senior News Editor (Fashion & Beauty)

Halie LeSavage is the senior fashion and beauty news editor at Marie Claire, where she assigns, edits, and writes stories for both sections. Halie is an expert on runway trends, celebrity style, emerging fashion and beauty brands, and shopping (naturally). In over seven years as a professional journalist, Halie’s reporting has ranged from fashion week coverage spanning the Copenhagen, New York, Milan, and Paris markets, to profiles on industry insiders including stylist Alison Bornstein and J.Crew womenswear creative director Olympia Gayot, to breaking news stories on noteworthy brand collaborations and beauty launches. (She can personally confirm that Bella Hadid’s Ôrebella perfume is worth the hype.) She has also written dozens of research-backed shopping guides to finding the best tote bags, ballet flats, and more. Most of all, Halie loves to explore what trends—like the rise of doll-like Mary Janes or TikTok’s 75 Hard Style Challenge—can say about culture writ large. (She justifies almost any purchase by saying it’s “for work.”) Halie has previously held writer and editor roles at Glamour, Morning Brew, and Harper’s Bazaar. Halie has been cited as a fashion and beauty expert in The Cut, CNN Underscored, and Reuters, among other outlets, and appears in newsletters like Selleb and Self-Checkout to provide shopping recommendations. In 2022, she was awarded the Hearst Spotlight Award for excellence and innovation in fashion journalism. She holds a Bachelor’s Degree in English from Harvard College. Outside of work, Halie is passionate about books, baking, and her miniature Bernedoodle, Dolly. For a behind-the-scenes look at her reporting, you can follow Halie on Instagram and TikTok.