Zendaya's Most Daring Outfits

There is more to fashion that just cleaning up well, throwing on an expensive designer suit, and posing for the shutterbugs. Much like acting, it's an art form with meaning, as Zendaya proves with every showbiz appearance she makes. For the last many years, the Emmy-winning star has been stirring things up in the fashion department just as brilliantly as she has in the cinema side of things. Her newfound status as a style revolutionary is not unfounded — authenticated by her historic win as the CFDA's youngest Fashion Icon ever, but also by her steady commitment to her role as a vessel of bold fashion expression. 

"There's nothing she won't try. She's fearless," stylist and image architect Law Roach told People. "Zendaya's always been my partner in going out to the event and telling a story without even opening her mouth." Sure enough, Zendaya and Roach's reputation as a formidable team on the red carpet is only gaining steam with each passing event. They have chucked fashion's foolproof rules of playing it safe out the window, instead pushing the limit of convention with exhibitions that are dramatic, brave, and even sensational. Here's a roundup of Zendaya's most daring outfits. 

Zippers on a gown? Sounds dubious. But hey, if Zendaya says it works, it works. The trendsetter was a heavenly vision in white at Paris Fashion Week 2023, arriving for a Louis Vuitton runway show in an exciting outfit that became the talk of the season. It was a longline gown accented with gold chain and buckle detailing that added character to an otherwise monochromatic color theme. The double zipper down the front, however, was easily the dress' boldest element — and Zendaya made judicious use of it by leaving only a fraction of it zipped up near the torso to hold everything together. 

The glaring low-cut neckline and high-cut thigh slit would have anyway left little attention to be spared for Zendaya's hair, makeup, and jewelry, which the star kept simple. It was a good serve from Zendaya. So good, in fact, that it led British Vogue to reward it with the title of "The 2023 Equivalent Of Liz Hurley's Safety-Pin Dress." For the uninitiated, the reference is to the legendary black Versace dress that actor Elizabeth Hurley wore back in 1994. With big bold safety pins holding it together — much like Zendaya's zippers — it assumed a status as the mother of all sexy dresses. So a comparison to it is basically the highest stamp of approval Zendaya's white dress could get. 

It takes one queen to know another. Hollywood's reigning superstar Zendaya paid a memorable tribute to music legend Beyoncé at the BET Awards in the best fashion possible — quite literally. The "Euphoria" actor showed up for the 2021 event in a barely-there purple dress that turned heads for more than one reason. The first, of course, was on account of Zendaya looking absolutely stunning. Secondly, there was no mistaking the infinitely iconic inspiration behind it. The low-plunging Versace number was the same one Beyoncé wore to the 2003 edition of the same award show, where she set the stage on fire with an unforgettable rendition of her then-fresh chart-topper "Crazy in Love." 

The purple dress left a deep imprint on public consciousness as one of Beyoncé's best looks of all time – and few other than Zendaya could have shouldered that legacy. In collaboration with her ever-dependable stylist Law Roach — who gave himself a deserving shoutout on Instagram for dipping into the fashion archives — Zendaya pulled off this vintage Versace with such panache that it won praise even from Beyoncé's mother. Tina Knowles took to social media to upvote Zendaya's look, revealing how back in 2003, she had personally snipped a few inches off the dress' original ankle-reaching hem for her daughter's BET Awards performance. 

Having fun with outfits is one way to kickstart the launch of a film. And nobody does it better than Zendaya. The undisputed queen of dressing to the nines, the Hollywood icon rarely misses an opportunity to incorporate some symbolism into her outfits. This diligence usually means that her film premieres are as much an exhibit of her acting chops as they are of her creative fashion sensibilities. At the Los Angeles premiere of Marvel's 2021 feature "Spider-Man: No Way Home" for instance, Zendaya channeled the theme of the superhero film by opting for a gossamer-like gown that had cobweb designs splattered all across it. 

The skin-baring Valentino creation flaunted a deep neck, a low back, and a high slit — all of which Zendaya conducted with MJ-like cool. We're not sure how the dress' many risqué cuts stayed in place but Zendaya's confident mien had us convinced that there was no room for a wardrobe mishap. The icing on the cake was an accessory she briefly had on — a feathered mask that referenced the iconic silhouette of Spider-Man's own. As Zendaya posed for pictures with Tom Holland — who had on a suave but simple brown suit — there was little doubt about who stole the show that night. 

Zendaya has no bad angles — and neither do her outfits. The Emmy-winning star was a vision to behold at the 2021 Ballon d'Or red carpet in Paris, where all eyes were as much on her superstar looks as they were on her exquisite dress. The vintage Roberto Cavalli piece, fished out of the luxury label's 2000 collection, was all-black save for some open-back gold detailing that stole the show. A column of shiny vertebrae held the dress together all the way from the top to Zendaya's lower back, from whence the figure-hugging dress picked up all the way down to the floor.  

Fans were convinced that the skeletal embellishment — which resembled the futuristic tentacles of Doctor Octopus, a major adversary to Spider-Man – was Zendaya's way of paying tribute to Marvel's superhero franchise, of which she has been a part since 2017. Honestly, one didn't have to squint too hard to see the likeness. Even the actor appeared to indulge the theory by re-sharing an Instagram post that made this pictorial comparison, writing, "We love a reference" (via Us Weekly). This cinematic wink didn't entirely come as a jolt, what with the release of "Spider-Man: No Way Home" around the corner at the time and Zendaya's well-known penchant for dressing to the theme of her films. A true creative, if ever there was one.

Leave it to Zendaya to wear a breastplate to a red carpet. In a look that can only be described as celestial, the "Euphoria" star arrived at the 2020 Critics' Choice Awards strapped into a hot pink metallic top and a co-ordinated skirt that constituted more an armor than an outfit. She may have not bagged the Best Actress award for her leading role as Rue Bennett on the drama series, but she sure won the night with her avant-garde Tom Ford breastplate. (Special shoutout to her bum-grazing braids!) 

It wasn't the first the world was seeing of that chrome fuchsia cutout; it had actually made its Hollywood debut a few days prior to Zendaya's red carpet showcase, when actor Gwyneth Paltrow posed in it as the cover star of Harper's Bazaar's February 2020 issue. The "Emma" star was seemingly ecstatic about the piece's return, writing on social media, "Thank God I can say I have something in common with Zendaya." 

Zendaya's wasn't an exact replica though, with the young actor revealing that she was custom-fitted for her breastplate. "They came to my house and I stood topless in my living room, while they had this machine that scanned my boobs," she told British Vogue. She also laid to rest the internet's ever-present questions about the (dis)comfort of wearing such outfits, saying that the metal turtleneck came with an absorbent lining that took care of sweat. 

Too much of a good thing is ... not necessarily bad — especially when it comes to Zendaya. Hollywood's hottest young icon turned up the heat at Paris Fashion Week 2022 in an all-pink ensemble that could have given Barbie a run for her money. Even against the Valentino show's fuchsia theme, the luxury brand's ambassador managed to stand out in her co-ordinated sweeping trench coat, floral appliqué trousers, and plunging blouse. 

All that hot pink could have been an overkill but the way Zendaya held her poise, she convinced us it was not, living up to the regard Valentino's top bosses hold for her. "She is aware of her bodily presence and she matches it with a radical romanticism that is completely aligned with everything we are doing in our brand," creative director Pierpaolo Piccioli told Women's Wear Daily.

Her fuchsia glam seemed like a bold choice. Except, Zendaya has been known to rock pink suits in the past. She took the "Good Morning America" stage by storm in that armor not once, but twice — first in 2017 and then again in 2021. The former was a baby pink joyride from Dundas, while the other was a well-tailored woolen number from Alexander McQueen. It's safe to say that Zendaya has all but established herself as the queen of business casual. 

Like a true artist worth their salt does, Zendaya gets into the skin of her characters as profoundly as she can — and she doesn't discriminate. Her commitment comes equally for Oscar-winning films like "Dune" as it does for animated bonanzas like "Space Jam: A New Legacy." The latter — for which Zendaya voiced the classic character of Lola Bunny — failed to land with critics when it was released in 2021. But the actor just about made up for this failed film moment with a fashion moment that was delightfully true to character and deserves to go down in the books as one of her boldest. 

For the premiere of the live-action comedy, Zendaya showed up in a long-sleeved jacket and micro shorts combo popping with cartoon colors. The tribute to her Looney Tunes character was evident, not just in her colorblocked Moschino ensemble but also her hair, which was swept up into Lola Bunny's signature high ponytail. The look was a medley of curious red carpet choices — from the hot pants to the graphic colors — and Zendaya pulled it off with great fun as only she could.