Zendaya Changes From Off-Duty Tennis Basics to Spring Glamour in Less Than 24 Hours

For four weeks straight, Zendaya has embodied all things tennis ahead of her upcoming project, Challengers. From literal on-court references to homages to the sport's all-time greats, she and her stylist, Law Roach, have done it all—or so fans thought.

Less than a week before the highly-anticipated film hits theaters, Zendaya made back-to-back surprise appearances in New York City in less than 24 hours. And in her unexpected sightings, she embraced her inner tennis star on opposite ends of the style spectrum.

Z's first appearance came last night on Monday, April 22, at a special screening of the movie. While eager guests hit the AMC theaters in Kips Bay for the private event, Zendaya surprised the crowd in a low-key outfit.

Pangaia Cotton Trench Coat

Everlane Way-High Drape Pant

Dear Frances Balla Mesh Flat

Her outfit for the evening included a crucial piece from the Challengers wardrobe: a gray “I Told Ya” graphic T-shirt worn by her character, Tashi Duncan. The cast has also sported the same tee, including her co-star Josh O'Connor—who plays Patrick Zweig in the film—who previously wore the shirt at the London premiere on April 10.

The tee, made by Challengers costume designer and Loewe creative director Jonathan Anderson, paid homage to John F. Kennedy Jr. The late politician wore a similar shirt several times, including while outside playing frisbee with his dog and his wife, Carolyn Bessette Kennedy. The phrase is suspected to be connected to the tagline his father, President John F. Kennedy, used for his inaugural buttons, reading "I Told You So" in red letters.

Zendaya styled her T-shirt with black wide-leg trousers, white pumps, and a brown trench coat. For the night, she wore her freshly dyed honey-blonde hair down in loose retro waves and finished her glam with a light peachy finish.

"When JFK Jr. was younger, in the '80s and '90s, there was kind of an effortlessness to his wardrobe—like he could wear anything, and sex appeal would always be there," Anderson told WWD about his source of inspiration for Zendaya's easygoing shirt.

Zendaya's JFK reference wasn't the only statement she made in New York City. Early next morning on Tuesday, April 23, the actress was seen heading inside to film a segment on Good Morning America. Unlike the ultra-relaxed look she sported last night, she went springtime glam instead.

She wore a white midi dress from Erdem's Fall/Winter 2024 collection, featuring green and white florals throughout. The actress trimmed the skirt to be slightly shorter, revealing the puffy tulle liner underneath. She styled her look with matching white stilettos and wore her blonde hair down with a side part and in loose waves.

Following her appearance on the talk show, Zendaya changed into a vintage Thierry Mugler suit and coordinating Louboutin pumps. It was her most court-adjacent look of her New York City stop so far, thanks to the neon tennis ball hue of her suit and shoes. As with her previous looks, Zendaya accessorized with Bulgari diamonds.

If there's anything fans have learned from Zendaya and Law Roach over the years—and as seen from their previous Dune press circuit—it's that the duo isn't done until they say they're done. This means that there may or may not be getting a few more Challengers-inspired looks leading up to the release day—and fashion lovers are not complaining!