Zendaya Ends Her 'Challengers' Fashion Tour With a Williams Sisters Homage

She copied one of the Grand Slam-winning pair's first photoshoots down to the hairstyle.

Zendaya sits on a couch wearing a black and white Carolina Herrera gown to reference Venus and Serena Williams in Vogue
(Image credit: @luxurylaw)

Zendaya and image architect Law Roach saved their most poignant Challengers press tour serve for last.

Days after the Challengers Los Angeles premiere, Roach shared two photos of his star client dressed to pay homage to an early Venus and Serena Williams Vogue photoshoot. Zendaya's look consisted of a square-neck Carolina Herrera gown with exaggerated black and white stripes, paired with shoulder-length beaded braids. It's a detail-for-detail replica of the Williams sisters' matching Herrera dresses for their 1998 editorial with photographer Annie Leibovitz.

A post shared by Law Roach

A photo posted by luxurylaw on

On Instagram, Roach thanked Carolina Herrera creative director Wes Gordon for designing the replica gown. "An ode to the GREATS," he wrote, tagging Venus and Serena Williams. "We thank you for all you have done!"

To match Venus and Serena's 1998 hairstyles, Zendaya tapped Kimble Haircare for a custom wig which was then styled by Ursula Stephen. Longtime makeup artist Ernesto Casillas handled her strong eyeliner and glowy skin; he also took Zendaya's photos.

Serena and Venus Williams wearing braids with beads on a tennis court

Venus and Serena Williams in 1998, the same year of their Vogue editorial in matching black-and-white striped gowns.

(Image credit: Getty Images)

With their recreation, Zendaya and Law Roach gestured at a turning point for two of tennis's greatest-ever players. In 1998, Venus and Serena Williams were 17 and 16 years old, respectively. Their stars were rising on the international tennis circuit; that year, they would also play against each other professionally for the first time, in the Australian Open. Their Vogue photoshoot also set the stage for a career-long relationship with fashion, which would take the sisters to the front rows of fashion week and into campaigns with major luxury and sportswear brands.

Zendaya's custom Carolina Herrera look concludes a four-week fashion marathon where no tennis reference was too literal. The actress embodied her character, Tashi Duncan, in everything from glittering Loewe tennis dresses to a string of Wimbledon white gowns by Louis Vuitton, Thom Browne, and Calvin Klein. The final premiere went in a different direction, pulling a deconstructed Vera Wang gown out of Roach's archives (perhaps to match with the pink and black color scheme of the Challengers carpet).

Zendaya at the Challengers Rome premiere in a white Calvin Klein suit set

Zendaya's Challengers press tour was defined by all-white gowns referencing "tennis whites," by a range of European and American designers.

(Image credit: Getty Images)

Zendaya on the 'Challengers' Los Angeles premiere red carpet wearing a deconstructed Vera Wang gown

For the final stop, Zendaya had broken her pattern of overtly tennis-inspired dresses with a deconstructed Vera Wang ballgown.

(Image credit: Getty Images)

What better way to end the one of the greatest press tours of all time than with a nod to its ultimate inspiration? No one knows the intersection of tennis and fashion better than Venus and Serena Williams.

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.