Zendaya's Biggest Fashion Risks We'll Never Forget

In today's colorful and extravagant fashion world, few names stand out as true fashionistas — those who can pull off the most bizarre and incredibly fashion-forward items without losing an ounce of their confidence. And one of those figures is undeniably Zendaya. The multi-talented icon is known for always giving us her best at industry events and movie premieres, and plenty of her looks have become a major part of fashion history.

With her stylist, Law Roach — with whom she's been collaborating since she was just 14 — Zendaya has carved her way into the fashion world, inspiring so many others with her unique and eclectic choices. "We made a pinky swear that I would do everything to help her grow, and as she grew, she would bring me along with her," Roach told Today following the 2024 Met Gala. "She kept her promise. Our loyalty is not something seen much in this industry." Now, while most agree that she's the most fashionable star of her generation, her journey has had its fair share of risky moments. 

Zendaya's futuristic robot-inspired look at the world premiere of "Dune: Part Two" has truly set the standard for risky outfits. Embracing a vintage Mugler creation from 1995, the star walked the red carpet in a shiny silver bodysuit that gave us major fembot vibes. The risk? Well, it's quite literally a balancing act. The metallic bodysuit looked impressive, but it also seemed like an outfit that could easily fall apart with one wrong move, and the shiny silver material could've come across as too costumey. 

The star admitted that wearing the outfit wasn't easy. "The metal conducts and holds onto heat very quickly and kind of traps heat in," she explained to Vogue. However, with careful planning, she made it work: "I'm wearing a complete body suit so there's a barrier ..." Law Roach also spoke about the significance of the outfit. "It was a dream to touch it, let alone get approval for her to wear it the way she wore it," he told the outlet. "Jean-Jacques [Urcun], the guy who actually crafted it with Mr. Mugler, was in our fittings; he helped dress her the night of." 

Zendaya's oversized hat at the Teen Vogue party in 2014 is still remembered as one of the most controversial fashion moments of her career. Rocking an Emporio Armani hat that somehow defied the laws of gravity was definitely a very risky choice. Oversized hats can (and at the time, hers did) look ridiculous. 

Of course, wearing such a large hat isn't just a style risk; it also comes with its fair share of practical challenges. The danger of it falling off, despite surely being carefully secured, was very real. And let's not forget how uncomfortable it must have been to carry such a weight on her head all night. "This, this was a controversial look," she admitted to Vogue. "I still see memes about this particular look with my hat, but you know what — I stick by it. Me and Law, we thought it was chic at the time. I think it's still chic," the former Disney star said. "Might have to bring it out of the archives one day." What seemed daring and unconventional back then now stands as a testament to Zendaya's eye for fashion, proving just how ahead of the fashion game she and Roach have always been. The hat was pushing fashion boundaries — and isn't that what fashion's all about?

At 2024's Essence Black Women in Hollywood Awards, Zendaya decided to go for a more relaxed and retro red-carpet look, pairing baggy jeans with a delicate Jean Paul Gaultier lace corset and pointy heels. Of course, everyone knows that jeans aren't typical red-carpet attire and can easily look too casual. But Zendaya ensured it was interesting by adding a unique twist to the throwback look. She accessorized with a statement silver choker that covered her entire neck, two chunky silver cuffs, and layered silver belts.

Law Roach revealed their approach to fashion to Vogue in 2024, highlighting Zendaya's tendency to favor throwback and retro styles. "We never work based on what we think somebody's reaction is going to be," he admitted. "We've been [using vintage] since Zendaya and I began working together ... At first, it came out of necessity because back when we started, nobody would lend her clothes. And I come from vintage — I had a vintage store in Chicago — so a lot of the things that she wore were things from my store or vintage pieces." 

Zendaya's "Dune" red carpet looks are truly unforgettable, and with the second part of the franchise, her fashion choices became even braver. "For the first [press tour], I hadn't seen the movie, so I did everything just based off the trailer," Roach admitted to Vogue in 2024. "This time around, I knew what to look for." 

At the Seoul premiere for "Dune: Part Two," Zendaya rocked a gray jacket with red detailing and its matching skirt — both from a Givenchy 1999 collection by the late Alexander McQueen. Roach revealed what it was like to dress the star for the movie's press tour: "We adopted method dressing," he explained. "The looks served as an extension of the wardrobe from the movie. It was intentional and purposeful." The best part about this stunning ensemble was the red pattern which looked similar to a motherboard, and it was glowing in the dark. Of course, a glow-in-the-dark look could have easily been too much, but not with Zendaya. "The appliqués are filled with a liquid, and that's what happens when the light hits it," Roach added.

In 2015, Zendaya opted to have her hair styled in locs for the Academy Awards — a traditional African hairstyle that served as a significant statement at the most prestigious event in the industry. Giuliana Rancic, a "Fashion Police" co-host at the time, said that Zendaya's hair looked as if it smelled of "patchouli oil or weed," a remark that showcased just how ignorant and unaware of the heaviness of her words she was (via W Magazine). For Zendaya, embracing a traditional hairstyle at an event like the Academy Awards wasn't accidental. "That's how change happens," the star told the outlet in 2021. "And it made me think, 'How could I always have a lasting impact on what people saw and associated with people of color?'"

Back in 2015, Zendaya responded to the remarks made by Rancic by writing on Instagram: "There is a fine line between what is funny and disrespectful. Someone said something about my hair at the Oscars that left me in awe. Not because I was relishing in rave outfit reviews, but because I was hit with ignorant slurs and pure disrespect." Zendaya's decision to wear locs to the Academy Awards was not only a bold fashion choice but also a powerful statement against cultural stereotypes and discrimination — one that was certainly needed.

Stepping out at the "Spider-Man: No Way Home" premiere in 2021, Zendaya wore a Valentino Haute Couture gown that was embellished with delicate black spider webs — a clear homage to the movie. The dress also featured a plunging neckline, low back, and a thigh-high slit that left us all without words. To make things even more interesting, the star decided to add a fun black lace mask, which she took off at one point.

Using fashion as a bold tribute to the movie's themes is something she and Law Roach have proven to be experts at over and over again. Of course, stepping out not only in a dress covered in spider webs but also wearing a themed mask could have easily been too much. However, Zendaya just ended up exuding a mysterious and intriguing vibe, making us want to watch the blockbuster immediately.

At the 2018 Met Gala, the theme was "Heavenly Bodies: Fashion and the Catholic Imagination," and Zendaya's choice of attire was daring and unexpected. The former Disney Channel star wore a Versace dress inspired by Joan of Arc, a symbol of female strength and power. She paired the dress with a chic and slightly messy copper bob, and the entire look was a modern interpretation of medieval-armor fashion.

The star's hairstylist Ursula Stephen explained to Marie Claire, "Zendaya's look was inspired by the power of Joan of Arc and the opulence of Versace, who dressed her this evening. The gown references armor and chainmail, so we knew we needed a strong beauty look as well." Pulling off Joan of Arc-inspired attire without looking like you're part of a theater group isn't easy, especially at an event as prestigious as the Met Gala. However, Zendaya managed to strike the perfect balance between high fashion and historical inspiration. However, a look like this didn't come without consequences. "I was struggling," Zendaya told Vogue. "I was like, 'I need to sit down.'"

For the "Dune: Part Two" premiere in Paris in 2024, Zendaya once again showed that channeling the movie's aesthetic in her fashion choices paid off, even if doing so was risky. The actor opted for a Louis Vuitton outfit that highlighted her abs — an edgy set that consisted of a top with a chunky turtleneck scarf and a drop-waist voluminous floor-length skirt. Somehow, the look seemed both vintage and modern, a style combination Zendaya and Law Roach are known for.

"I referenced one of Nicolas Ghesquière's earlier Vuitton collections, around 2020," Roach said of the outfit to Vogue. "With the abs showing, it felt so young but still so much like 'Dune.'" And as always, Roach was absolutely right. Even though Zendaya has worn many "Dune" premiere outfits, somehow, each one gets even better than the previous one, meaning we can't wait to see how she approaches press for "Dune: Part Three."

Zendaya's fun butterfly fashion moment at the Australian premiere of "The Greatest Showman" is still one of her most unforgettable looks. The star wore a butterfly gown from Moschino, which she pulled off like it was her second skin, proving her ability to make even the most whimsical and quirky pieces look chic and anything but costume-like. The breathtaking gown featured a vibrant red-orange-yellow butterfly wing that extended from the bodice, creating a dress you just couldn't stop staring at.

She kept the rest of her look simple, allowing the intricate fashion piece to take center stage. With subtle and classy accessories and sleek hair and makeup, Zendaya let the gown do the speaking. Of course, her confidence on the red carpet made the bold and unconventional dress choice seem entirely natural — even though we can't imagine many others pulling it off.

Zendaya's changing look at the 2024 Met Gala proved she's a staple at the event, as it was a bold move that not many have dared to do. As a co-chair of the event, she had to make sure her looks were simply spectacular, and she certainly delivered. For her first look, Zendaya wore a stunning creation by John Galliano for Maison Margiela. The blue and green tulle, as well as the leaves and berries, perfectly fit the event's theme, "The Garden of Time." She completed the look with a striking avant-garde headpiece and grungy makeup. 

But Zendaya wasn't done yet. She returned to the carpet later in the evening to debut her second ensemble: a black off-the-shoulder gown, also by John Galliano, this time for Givenchy. Law Roach spoke about the significance of the moment to Today, saying, "For me, growing up, that's what I thought fashion was: John Galliano at Dior. It was a world I was captivated by, but I didn't think I could live in, breathe in, have space in. Last night was a celebration of the world that has inspired me for so long."

Black gowns are red-carpet staples, but they can easily look boring. However, Zendaya's strapless black Valentino gown at the 2022 Emmy Awards stood out thanks to its Old Hollywood charm. It was the perfect choice for the night where she once again made history by becoming the youngest actress with two Emmy wins as well as the first Black woman to win in the "Outstanding Lead Actress in a Drama Series" category twice (she previously won it in 2020, also for "Euphoria").

Law Roach revealed how the look came to be, telling Vogue, "We took inspiration from Grace Kelly and Old Hollywood movies. Zendaya and I were also really inspired by Valentino's fall 1987 collection. There was a red dress that Linda Evangelista wore in an editorial, and we took inspiration from the bodice of the dress — but we made it black and the skirt a lot bigger." Roach added, "I woke up in the middle of the night and called Valentino, asking them to make this new dress." The rest was, like Zendaya, history in the making.

Zendaya and Law Roach are undoubtedly excited about what the future of fashion has to offer, which is why it's not surprising that the two eagerly embrace any new technology and innovative design concepts in the industry. One of Zendaya's most memorable futuristic looks is the "La Robe Spirale," or the Spiral Dress, designed by Pieter Mulier for Alaïa.

The dress is not your typical gown — it was created with 3D-printed wool, wrapping around Zendaya in a spiral-shape. Zendaya and Roach chose this Alaïa look for her "Dune: Part Two" press tour, again perfectly complementing the movie's aesthetic. Roach shared his admiration for the dress with Vogue, saying, "I loved the process of how they created the Alaïa. It's 3D-printed, and that form was just so architectural and futuristic." As always, when she's wearing a piece that is stunning on its own, Zendaya decided to keep the rest of her look simple.

At the 2019 Emmys, Zendaya wowed us with gorgeous copper locks and an emerald-green gown that instantly reminded us of Poison Ivy. The Vera Wang dress consisted of a sheer-looking corset top and a silk skirt that draped all the way to her shoulder on one side. 

The risk in picking such a look stems from the fact that Zendaya hadn't completely ditched her Disney image until the release of "Euphoria." In fact, in 2016, Law Roach admitted that the two are very mindful of her fans when choosing fashion pieces. "I think we're both very conscious of who her audience is and who looks up to her," Roach told W Magazine. "She's very responsible in that matter ... She has a huge respect for the younger girls who've grown up with her and the ones who are discovering her now. One of the things we say is: You have your whole life to be sexy. So, that's one of the things she hasn't really done." And if there's one thing this emerald-green Vera Wang creation is, it's unapologetically sexy.

While the wet-look trend has been thriving for a couple of years now, not many have delivered on it as flawlessly as Zendaya. For a "Dune" premiere at the Venice Film Festival in 2021, the star wore a leather dress by Balmain designed by Olivier Rousteing, exclusively for the actor. "The bespoke leather gown was crafted using an exact model of the star's bust, taking full advantage of the Balmain atelier and the house's artisanal tradition," the luxury brand revealed in a press statement.

While the dress alone would ensure Zendaya was in the spotlight, the star decided to pair it with statement jewelry — a chunky Bulgari necklace whose emerald-green color perfectly complemented the nude gown. Of course, no wet look is finished without the perfect hairstyle, and Zendaya's subtle wet hair waves were a fitting choice.

Zendaya and Law Roach's 2019 Met Gala was for some a huge hit, and for others, a total miss. With "Camp: Notes on Fashion" being the night's theme, the two channeled a fairytale — Zendaya was wearing a Cinderella-inspired gown by Tommy Hilfiger while Roach was dressed like her fairy godmother. And while Zendaya has since then proven that she is capable of wearing costume-like pieces without giving Halloween, this look was undeniably going for the costume aesthetic. Of course, for the camp theme, this was not only acceptable but expected.

Apart from the costume aspect, the look was significant due to Zendaya's ties to the Disney Channel, where her career kicked off in 2010 thanks to the sitcom "Shake It Up." "[It's] the total opposite of every character I think she's ever played and a huge stretch from 'K.C. Undercover,'" Roach revealed to Vogue. "It's almost like this is the last hoorah and the last time people will identify her as a Disney princess — which isn't a bad thing. It has to be literal enough so that people get it." He went on to explain, "When you see Cinderella, you know right away it's her; the baby-blue dress and the hair and the French twist it all works together."