Zendaya Holds Court

This is what happens when you ask Zendaya, of all people, about her worst fashion looks. She has to enter a time machine and go all the way back to her first press tour for her Disney Channel show Shake It Up in 2012. She Googles “Germany Zendaya” and presents her iPhone to me, showing me a photo of her leaning against a glass railing in Munich, wearing flared pants and a Waldo-esque striped cardigan with an aqua blazer and yellow tee. At the time, she didn’t have a clothing budget. But she did have Law Roach.

“I’m angry at him to this day,” Zendaya jokes. “Like, why would you put me in this? Bitch, you could’ve done better!” She laughs. The outfit was among her first collaborations with Roach, her longtime stylist, whom she met through a family friend when she was 14 and Roach was running his Chicago boutique, Deliciously Vintage.

Sitting across from me at a table in a private back room at Crossroads Kitchen, a high-end vegan restaurant in West Hollywood, Zendaya grabs her phone to share another photo of the very first outfit Roach ever picked out for her: a chrome-colored metallic blazer and miniskirt combo she wore to Justin Bieber’s 2011 Never Say Never documentary premiere that she considered “edgy” as a teen and now admits is cute. Back then, Zendaya wanted her styling to be age-appropriate, so even her juvenile ensembles are more adorably nostalgic than questionable.

I ask for an example of when she started taking more risks on the red carpet. She points to 2014, recalling a black Emporio Armani jumpsuit Roach styled her in, paired with an oversize bowler hat that rightfully earned mixed reviews, inspiring headlines like “Who Wore a Super Huge Hat Better: Zendaya or Lorde?” “People were like, ‘Oh no, Zendaya’s gonna start looking like this now,’” she remembers, adding that she and Roach still love that look anyway.

Reminiscing with Zendaya about fashion stumbles she made (and still pulled off) when she was practically a baby reminds me of how much she’s grown up in the public eye. Over time, we’ve seen her go from charming tween ’fits to statement-making, Roach-styled looks that make you wonder if God is their personal tailor on Earth. But Zendaya’s style transformation is just one way she’s evolved past her roots. Under the luxe amber glow of a crystal chandelier, she explains that, on the cusp of 27, she’s entering an era of risk.

“From a character perspective, I want to find things that will push me,” she says. She’s dressed in a pair of belted, high-waisted jeans and a silky black button-up with sockless Chanel loafers and a sleek, wavy lob, parted down the middle. “As I get older, you know, I can’t play a teenager for the rest of my life.”

For years, the reliably mellow actress has occupied a singular position as a next-gen movie star and full-time fashion muse with a glint of old-Hollywood charm, which started with her breaking out from her cherub Disney days at 22 to star as a recovering but often spiraling teen addict, Rue Bennett, in HBO’s drama Euphoria. In 2020, she became the youngest actress to win an Emmy Award for Outstanding Lead Actress in a Drama Series, portraying a high schooler so fluently onscreen that she still reads as youthful to the general viewing public.

She’s so far chosen roles that optimize her unique Daria drollness, starring as a classic high school outcast in the Tom Holland–led Spider-Man franchise and an enigmatic character alongside Timothée Chalamet in the epic Dune (for a cool seven minutes). And yet, somehow, she’s never quite fully commanded the big screen like she does in director Luca Guadagnino’s R-rated tryst drama Challengers—a feat of sensual chaos that Zendaya describes as her “first time really being a leading lady, if you will.” Her character, Tashi, is a Serena-like tennis phenom who becomes a coach after an injury and finds herself at the center of a love triangle with the two most competitive men in her life, played by co-stars Mike Faist (as Tashi’s husband, Art) and Josh O’Connor (as her ex-boyfriend, Patrick). It’s a movie about tennis, but not really—it’s more about the consequences of failure on a global stage.

The role is a significant departure for Zendaya, a chance for audiences to see her in a whole new light, playing a quietly cutthroat femme fatale in a film with very adult stakes. It’s the type of performance she knows fans are ready to see from her (“More ready than I am,” she jokes). At the same time, it’s not an unbelievable volte-face. Her subtle performance of seduction onscreen makes the evolution feel more authentic than forced. “I felt like it was a good step into a more, I guess you could say, ‘grown-up’ role and into that next phase,” Zendaya says. “It was a little bit scary to take on, which I think is a good feeling. To be like, ‘Ooh, can I do this?’ You could run from that feeling and stay safe and comfortable, or you can go, ‘You know what, fuck it.’”

Challengers has the familiar tense, erotic undertones of a Guadagnino picture (think 2017’s Call Me By Your Name), with a timeline that jumps from high school to college to thirtysomething, allowing Zendaya to exercise the range the director wanted. “Zendaya is a wonderful partner to work with,” Guadagnino says. “The way she expresses and exudes the power of her athleticism is wonderful, but at the same time, the way she goes through seduction is very beautiful in the film.” While some of the sex scenes are intense, they’re in line with Zendaya’s own views on sensuality as an implicit language. “It’s what Luca does so well. It’s the things that aren’t. It’s the moments between the moments. Like, chemistry. The things that you can’t always say, but you feel,” she explains. “That is Luca’s specialty when it comes to filmmaking. All the things that aren’t on the page that only someone who’s got the camera can really find.”

Our interview, conducted prior to the SAG-AFTRA strike, is the first time Zendaya says she’s talked about Challengers in depth to a stranger, and she’s stuck figuring out Tashi’s motivations. “I still don’t understand the decisions she makes, and we had so many conversations about the psychology of her and why she is that way,” she says. “What was important to me was that she was unapologetic about it. Sometimes characters who are messy and conflicted and wield power over other people are reserved for [actors] who don’t look like me, so when I get an opportunity to play a character like that, I’ma take it!”

O’Connor says Zendaya masterfully captures Tashi’s tragic ferocity. “It’s mad how she did it. You really feel sorry for her, like, oh my God, poor Tashi. But hang on a minute, she’s got these boys under her thumb. She’s in complete control over them,” he says. “I look back on her other projects—they’re all so detailed and different. She’s not resting on her laurels, so for me, the surprise was that everything she did in Challengers felt like a new idea.”

You could say Zendaya is fairly familiar with the idea of a teenage superstar feeling pressure to succeed. Still, it surprised her how self-conscious she became on set. After three months of tennis training (she hops up from her seat to demonstrate the footwork she learned), she developed a new appreciation for athletes who compete and perform at the same time. “The more I had to pretend to do tennis in front of a camera with an audience, the more terrified I felt. And I was not even using a real ball,” she says with a laugh. “I’m just doing the form and footwork and getting my swing right and doing it in front of a whole bunch of people as if it’s the US Open, and I’m terrified.”

While filming in Boston in the spring of 2022, Zendaya started noticing how much more famous she’s become in a short span. Even for an actor who’s been a mononymous household name for half her life, every level of fame involves a recalibration. “After the last Spider-Man and the last season of Euphoria, there was a visceral change,” Zendaya explains. “Before, I could get away with going places and getting in and out. But in Boston, I would end up going right back home, because it was really overstimulating. Everybody would go hang out at a bar or something, and I’d be like, ‘I’d love to, but I think I could ruin everybody’s night. Because it’s just not going to be fun once I’m there.’ ”

She remembers a store run for a pillow that ended with customers taking pictures of her at the register while dealing with a card issue. “I was just like, Why? You see I’m flustered,” she says with a snicker, taking it in stride. Again, while in Italy a few weeks ago, she was photographed walking her dog, Noon. “I had this idea of, like, I can walk around Venice. No, I can’t,” she says, laughing sweetly. “I had to pick up his poo, and I was like, Lord, please, don’t take a picture of me picking up my dog’s shit. There’s a picture of me holding the bag, but thankfully they spared the grabbing and the putting it in the bag part.”

I mention seeing a photo of her and Holland on a boat ride in Venice and ask if it helps that at least the interest comes from fans who see their relationship as adorable. There’s no Scandovalian salaciousness, so maybe it could be worse. “Parts of my life, I accept, are going to be public,” she says. “I can’t not be a person and live my life and love the person I love. But also, I do have control over what I choose to share. It’s about protecting the peace and letting things be your own but also not being afraid to exist. You can’t hide. That’s not fun, either. I am navigating it more than ever now.”

Zendaya is now on my laptop, styling my Sims 4 character, Lyric Miles, as a challenge. She hasn’t played the game in years and is struggling to find a look that doesn’t clash with my Sim’s shoulder-length, electric-blue sideswept hair. “You could have a Y2K moment,” she suggests, pairing a hot-pink, prom-ready tube top with a bright, highlighter-yellow skirt. Even the Sim seems disappointed with the limited options.

“I’m gonna need them to get this together a little bit,” Zendaya says, laughing. “If we keep the top simple, maybe we can do a fun pant moment.” Scrolling past a palate of busy patterns, she lands on an outfit I previously styled when I first created the Sim: jeggings with an oversize forest-green graphic sweatshirt, a gray beanie, and dark brown booties. “That’s perfect! I love this,” she says, validating me. “It feels like her.”

Zendaya’s emotional attachment to fashion comes partly from her mother, who at 6’4” had to have clothes custom-made. “She was always made to feel like she couldn’t enjoy certain fashions because they literally didn’t make them for her or because people always made comments about her height, and she was self-conscious about it,” Zendaya says. “I also felt like there was part of her that loved fashion. But it was hidden. I think she vicariously lived through me experimenting.”

Growing up a shy theater kid in Oakland, Zendaya dressed herself in the weirdest rhinestones and mismatched threads she could find. Her parents encouraged their daughter’s sense of playfulness. Her grandmothers were glamorous and let her rummage through their closets, where Zendaya would tie their slipdresses tight in the back to fit like a gown and pose in her maternal grandmother’s vintage jewelry. She remembers helping her paternal grandmother, now 94, paint nail polish on her shoes to match her church outfits. Zendaya reaches over the table to show me an iPhone photo of the shrine her paternal grandma has of Zendaya’s magazine covers and editorials in her Oakland bedroom.

While Zendaya has settled into a position as a sought-after trendsetter—scoring brand ambassadorships with top names such as Valentino, Lancôme, Bulgari, and Louis Vuitton—Roach has flourished alongside her, bringing the celeb stylist’s point of view to the forefront. So when Roach announced his retirement in March, citing in part industry politics, it was ominous. Earlier that month, a video of him confusedly searching for a seat next to Zendaya at Louis Vuitton’s Paris Fashion Week runway show had gone viral. Fans interpreted her body language as her dismissing him and worried the two had split.

Roach later cleared up the rumors and said that their relationship was beyond solid, but that he was still figuring out his new title. Over the phone, he confirms he’s stepped into an official role as Zendaya’s creative director and tells me, “Our relationship is like family, so I don’t think I’m going anywhere—and even if I wanted to, she wouldn’t let me.”

She watched the seating mishap become a thing online. “When it happened, I said, ‘Oh no, I hope people don’t try to create something from this,’” she says. Her recollection of the show is the same as Roach’s. They had gotten stuck in traffic and then were rushing to the front row. After Zendaya was seated, she says they tried to find Roach’s assigned seat. You can’t hear audio in the video, which shows her pointing to a row behind her, as if suggesting that’s where Roach should sit. The truth is that she was pointing to her assistant Darnell’s seat. But some viewers who saw the clip assumed Roach was offended. “We’re so used to sitting together that he didn’t know where to go,” Zendaya clarifies. “But obviously, people want to assume the worst of the situation, which is not always easy to deal with and hurtful.”

It was a classic example of the internet overanalyzing a few seconds of mayhem. Roach maintains that Zendaya has firmly supported his growth. “I’m grateful that people like the work and understand the story. And I’m grateful for her giving me the opportunity to shine,” he says. “It’s not often that such a big superstar like that is very generous and understanding when someone wants to basically step out. She’s been one of my biggest supporters.”

The assumption that Zendaya had somehow prompted Roach’s retirement was a stretch. He’s since continued to style her for red carpets like Bulgari’s mid-May jewelry event in Venice, as well as the shoot for this magazine and her Louis Vuitton campaign debut this spring. “I ride super hard for my team, especially for people I love,” Zendaya insists. “He’s involved in every fashion contract, everything I do. If I have an opportunity where he can come with me, he’s always going to be there. He’s always been my creative director in a sense, and he continues to fill that role, because it’s more than just clothes on a red carpet. It’s a bigger thing.”

Thirty minutes into our nearly three-hour lunch, Zendaya interrupts the conversation to ask me if I’d heard about Tina Turner. We’d both gotten the news that morning that the rock legend had died at age 83, and it had been in the back of our minds ever since. Zendaya discovered Turner through her grandma as a kid and was mesmerized. “What I love so much is the fact that she was a rock star at a later part of her life when they try to tell you that you can’t be desirable or still sell records,” says Zendaya, offering a tribute. “She had the biggest moments of her career in her mid-40s. It’s beautiful and proves you can evolve and keep doing it at any point in your life.”

In April, Zendaya joined British singer-songwriter Labrinth at Coachella, performing live onstage for the first time since she was a teen. It was a whole new experience, singing their collaborations “All for Us” and “I’m Tired,” featured in season 2 of Euphoria, surrounded by thousands of shrieking fans who knew all the lyrics. For the first time in a while, she had stage fright, which happens even to a performer who loves to scare herself into being bold. “She’s the most competitive person I know, in a good way,” Euphoria creator Sam Levinson says. “She’s constantly growing as an artist and always seeking a challenge. She’s never complacent.” (He adds that he sees Euphoria’s upcoming third season as a “film noir” and says, through Rue, he plans to “explore what it means to be an individual with principles in a corrupt world.”)

Zendaya released a debut solo album in 2013 and a handful of singles, but that night onstage, she’d never felt so exposed. “I have a lot of negative experiences with the music industry, and being onstage is really the worst,” she explains. “It carries a lot for me, and I was afraid to open that door again. But I was also like, ‘You can’t run away from this forever.’” Afterward, she posted a video about her excitement on Instagram Stories, where she said she couldn’t hear her own voice through her earpiece over the crowd noise and had no idea how she sounded. But at some point, she realized she had to let go.

“I had to be like, ‘Dude, take a second and look at how special this is. These people are giving you so much love and energy,’” she says. “I’ve never experienced that before. That blew my mind.” She goes into her inner monologue now, just Zendaya speaking to Zendaya. “I had to go, ‘Stop thinking about the fucking technical stuff. Like, it’s fine. Like, whatever. It’s not going to be perfect. You haven’t been onstage in front of that many people ever in your life. Enjoy the fact that you did it. You got over your fear. You did it, and these people enjoyed it with you, gave you love and energy, and were excited that you were there. That’s enough.’”

Hair by Kim Kimble at A-Frame Agency.com; makeup by Ernesto Casilla for Lancôme; manicure by Marisa Carmichael for Apres Nail; extras casting by Barbara Pfister; produced by Viewfinders; photographed on location at Ace Hotel Downtown Los Angeles.

This article appears in the September 2023 issue of ELLE.

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