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"Challengers" Milan Photocall© GettyImages

Zendaya revives Cindy Crawford’s Classic 1991 tennis dress for Milan appearance

The Euphoria actress continues her string of stylish sporty looks to promote her upcoming film, ‘Challengers’


Andrea Pérez
Deputy Editor Miami
APRIL 18, 2024 4:44 PM EDT

International media are closely following Zendaya during her promotional tour for  “Challengers,”   where she plays a tennis champion. Her outfits hint at what to expect when the movie directed by Luca Guadagnino premieres worldwide on April 26, featuring sporty staples like polo shirts and pleated miniskirts.

Watch the trailer for this tennis-themed rom-com

CHALLENGERS - Official Trailer 2 - Warner Bros. UK & Ireland

Zendaya traveled from London to Milan for the film’s photocall, where she continued showcasing several stunning looks. See below the latest two minidresses she wore.

"Challengers" Milan Photocall© GettyImages

Zendaya sports a ‘vintage’ look in Milan

This time, while in the Italian city, she revived a 90s retro sleeveless tennis minidress with a shirt collar and flared skirt from Polo Ralph Lauren.

Polos have been essential to tennis fashion since French champion René Lacoste designed his breathable, comfortable model in the 1920s.

Ralph Lauren introduced his polo in 1972, long after Lacoste’s success. Unlike the French version, designed for high performance, the American design was marketed from the outset as a symbol of aspirational American leisure.

Cindy Crawford© GettyImages

Cindy Crawford wore the same dress in 1991!

In the early 80s, the design became synonymous with the ‘preppy’ aesthetic, often linked to elite northeastern U.S. schools. The dress worn by the actress is an original from that era, when preppy fashion was booming, with its minimalism and simplicity.

The dress was from the Polo Ralph Lauren Spring/Summer 1992 collection, a subsidiary of the company. Cindy Crawford famously wore it on the runway as her career was transitioning from television and magazines to the fashion world.

"Challengers" Milan Photocall© GettyImages

Zendaya’s stylist: Law Roach

Law Roach, Zendaya’s stylist for over a decade, is responsible for diving into the archives of historic fashion houses to find authentic vintage treasures that the actress might wear at her premieres. It’s an approach he has used on many occasions and has earned the Euphoria star a legion of fans who admire her style and elegance, in addition to her acting talent.

"Che Tempo Che Fa" TV Show© GettyImages

Another white tennis-themed minidress

As evening fell, Zendaya appeared on the late-night show “Che tempo che fa” in a white minidress with thin straps. The dress, made from a fabric similar to terry cloth, pays tribute to vintage Wimbledon uniforms. A draped detail at the hem mimics a towel, tying back to tennis themes.

"Che Tempo Che Fa" TV Show© GettyImages

Focusing on the dress - not the accessories

Interestingly, Zendaya wore the same white So Kate heels from Christian Louboutin at each event of the promotional tour. It appears that her stylist, Law Roach, wants to highlight her distinctive short dresses rather than the accessories.