5 Times Zendaya Should Have Landed On The Worst Dressed List
There are two reasons fans check daily to see what Zendaya's up to: To see if there's any engagement news about her and beau Tom Holland and to catch up on the star's latest fashion moments. After all, the "Euphoria" actress has established herself as a style superstar, claiming the Council of Fashion Designers of America's Fashion Icon Award in 2021 — the youngest ever recipient, at age 25 — and even had a Barbie created in her honor of her 2015 Academy Awards Vivienne Westwood look.
Of course, she also has stylist Law Roach, whom she's been working with since 2011, to thank for her transformation from Disney tween star to envelope-pushing trendsetter. But even with his assistance to consistently land her on best-dressed lists, Zendaya still has the occasional fashion fail that has left us wondering who let that happen. Here are five times that the Roach-Zendaya magic didn't deliver.
When she looked like she was playing dress-up in grandma's closet
At the 2013 Keep a Child Alive Black Ball, Zendaya missed the mark by wearing a frumpy Dolce & Gabbana dress that looked like it would suit someone 50 years older. (She was 17 at the time.) The voluminous, elbow-length sleeves swallowed her slim frame, while the neckline was uninspired. And let's not forget the Tabitha Simmons shoes. The shade doesn't match the dress closely enough, but it wasn't a big enough contrast either. The booties either needed to exactly mimic the shade of the Dolce —or they needed to be a stark contrast. Something kind of close becomes distracting if it's on a fuller shoe, like a bootie. On a strappy sandal, it would've been less noticeable.
The Danielle Queller earrings and coordinating clutch were fabulous, and the makeup, with a bold lipstick and fully-rimmed black eyeliner, were spot on. Even the shoes are chic if judging them independent from the outfit. It's simply the dress that lets the look down. In something more age-appropriate and figure flattering, this would've been a winner.
When she wore an oversized bowler hat and elderly jumpsuit
The first element of this look, worn in 2014, that catches the eye is obviously the oversized Armani bowler hat, which Zendaya defended to Elle in 2023, saying it was a look "she and Roach still love." And she's right. The ensemble landed her plenty of attention at the time and even makes sense today for someone looking to make a statement. (The proof: personality hats were all the rage, as seen on the fall/winter '24 and spring/summer '25 runways at Chanel, Tolu Cocker, Gucci and Prada.)
But what's somewhat more troubling than the hat, is the actual outfit itself. This Emporio Armani jumpsuit might look fresh on a 50-something lady who lunches, but not on a teenager attending a Teen Vogue Young Hollywood party. Traditionally, Tinseltown's up-and-comers wear a lot of denim, leather, brightly colored and metallic mini-dresses, and other flesh-revealing ensembles to the event — not dowdy, long-sleeved, full-length jumpsuits.
When she wore an unflattering pirate look
Back in 2019, just as her acclaimed show "Euphoria" was becoming a sensation and she was promoting "Spider-Man: Far From Home," Zendaya was able to take a break to enjoy the play "Harry Potter and the Cursed Child." (She's a self-avowed Potter fan.) Yet, while the play was a hit, her outfit was not.
For starters, the proportions didn't work. By pairing a jacket that hit below the knee with jeans that are rolled up to meet boots at her lower calf, she essentially makes her lower half look cut up and shorter. It's simply not balanced. Then there's the matter of the jacket itself, which is meant to look intentionally distressed with thick white threads and rips at the waistline. Unfortunately, it simply looks sloppy when paired with casual jeans and a white T-shirt.
And finally, her glasses. In 2015, Zendaya told her followers on X, formerly known as Twitter, that she needed glasses. Since then she switches between glasses and contacts, though she rarely makes appearances in the former. While she's had plenty of moments where she looks stunning in her glasses, on this occasion the pair sat too low on her face, obscuring her stunning eyes and gorgeous cheeks. Don't worry, Zendaya fans, this moment wasn't a regular occurrence; her off-duty street style has come a long way since.
When she couldn't breathe in a C3PO suit
Zendaya is no stranger to method dressing, aka when a star's attire pays homage to the character they're promoting. Think: Margot Robbie promoting "Barbie," Jenna Ortega's looks on the "Beetlejuice" tour, and Blake Lively wearing florals as a tribute to her "It Ends with Us" florist role. For the February 2024 promo of "Dune: Part Two," Zendaya delivered in sand-hued and futuristic looks, including this metal suit, a vintage look from the Thierry Mugler 1995 runway collection.
While fashion aficionados and fans alike praised the risky move — just one of Zendaya's many daring outfits, this one missed the mark solely for practical reasons: She could have overheated and passed out. As Zendaya told Vogue, "Immediately after wearing it for 10 minutes, or less than that, I got, like, really light-headed." She explained, "The metal conducts and holds onto heat very quickly and traps heat in." That puts a whole new spin on suffering for fashion.
When she looked like Bardot gone wrong
Zendaya took her method dressing up a notch when she promoted her role as a tennis champion in "Challengers" in April 2024. With Law Roach's assistance, they created a cohesive wardrobe that played with the tennis theme: sometimes quite literally, with tennis balls on Zendaya's shoes or dresses; sometimes with the color palette, in tennis whites or in ball-hued optic yellow; and sometimes in the silhouettes, with polo-cut tops and tennis-skirt bottoms.
Unsurprisingly, Zendaya aced all her looks on the promo tour — except for one: a custom pink Jacquemus in Los Angeles. Other than the buttoned-up polo top, the tennis theme was lost with this ensemble. Instead of a confident pro, she looked more like she was trying to channel Brigitte Bardot or a fem-bot from "Austin Powers." The pink didn't feel right, nor did the ties at the waist, the bouffant hair with bow headband or the cotton candy shoes that coordinate with the whole outfit. It all feels too sickly sweet and not on theme at all. Thankfully, however, this look, along with the four above, are anomalies for Zendaya, who will undoubtedly continue to serve up the best fashion has to offer, whether it's promo tours, street style, red carpets or, dare we say it, walking down the aisle.