Zendaya re-wears Cindy Crawford's Ralph Lauren tennis dress for the runway at the "Challengers" Milan photocall.

Zendaya re-wears Cindy Crawford's Ralph Lauren tennis dress for the runway at the "Challengers" Milan photocall.

Zendaya's Challengers Tennis Fashion Tour has so far featured a number of custom court-inspired outfits, from racket-embellished Thom Browne dresses to ethereal Louis Vuitton gowns. At a photo call in Milan over the weekend, Zendaya and stylist Lo Roach decided to flip the made-to-order-only script by diving into the Ralph Lauren archives and borrowing a look last seen on legendary model Cindy Crawford.

Z appeared at the Challengers Step and Repeat in a short, fitted tennis dress with a polo collar and fluttery, billowing skirt. She paired the dress with her most frequently worn accessory on tour so far: white Louboutin heels and Bulgari jewelry.

Her country club-worthy look once again proved to be an incredible archival complement. Roach sourced this item from Ralph Lauren's Spring 1992 collection.

The vintage piece looked no more altered or accessorized with extraneous accessories than it did on its runway debut. Past and present, the styling is minimal, letting the fitted bodice and full skirt do all the work.

Zendaya, being Zendaya, borrowed a look from Cindy Crawford. On Saturday, spent courtside at the Monte Carlo ATP Masters Series in Monaco, Zendaya first appeared in a Brunello Cucinelli cable knit sweater and long-line skirt.

After a brief photo shoot, she changed into another outfit that would go down in fashion history. Her second look was a custom polo tank top tucked into a pleated skirt by athletic brand On. The item, which Lo Roach shared on Instagram, was inspired by the tennis wear worn by Althea Gibson, the first African American tennis player to win a Grand Slam in 1956.

Following red carpet appearances in Monaco and Milan, Zendaya added another twist to her tennis whites. Visiting the Italian talk show Che Tempo Che Fa, the 27-year-old changed into a custom-made toweling mini-dress by British label 16Arlington. She completed the all-white look again with her trusty Louboutin heels.

Zendaya's Grand Slam-inspired fashion days are coming to a close. The final stop on her tour appears to be the Challengers' Los Angeles premiere on Tuesday, April 16. According to the Instagram account @databutmakeitfashion, searches for "tennis fashion" have increased 80% this month.

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