Zendaya & Tom Holland's Worst-Dressed Moments As A Couple

Hollywood power couple Zendaya and Tom Holland are used to positive press and public praise, but even superheroes aren't immune to bad fashion days. They first met as co-stars in the Spider-Man franchise, but it did not take them long to transfer their on-screen romance into real life. And as their relationship progressed, they got plenty of opportunities to practice the tricky art of couple dressing.

Romance rumors linking the powerhouse acting duo started circulating as soon as the Spider-Man movies began filming, with some sources claiming their romance started as early as 2017, the same year their first movie together, "Spider-Man: Homecoming," was released in theaters. "They started seeing each other while they were filming Spider-Man," an insider told People in July 2017, the very month the film was released. "They've been super careful to keep it private and out of the public eye but they've gone on vacations with each other and try and spend as much time as possible with one another."

Despite these claims about Zendaya and Holland's relationship, the A-list couple did not confirm they were dating until years later in 2021. They went Instagram official that year a few months before "Spider-Man: No Way Home" hit theaters. The pair got engaged over the holidays in late 2024 and later had a secret wedding in early 2026. After spending a decade together both professionally and romantically, it is only natural that they had fashion mishaps along the way. From the first Spider-Man film to the latest, here are Zendaya and Tom Holland's worst-dressed moments as a couple.

Soon after they tied the knot, the newlyweds embarked on a promotional tour in June 2026 for "Spider-Man: Brand New Day." For a photocall in Amsterdam, they arrived in underwhelming attire that did not suit the movie's A-list stars. Tom Holland wore a standard navy-blue suit with a thin striped tie that could be seen poking out from the bottom of his jacket. The suit's pockets were unusually large, making it impossible not to stare at them. Meanwhile, Zendaya's Louis Vuitton outfit failed to impress the internet. "Usually love what Zendaya wears and she looks great is almost anything ... this outfit is cutting her body off at a weird spot and is just not very flattering. It doesn't look tailored well," a Redditor said as other users agreed.

During the German Fan Event for "Spider-Man: Brand New Day" in Berlin on June 22, 2026, the couple wore unflattering outfits while posing at the Amano Rooftop bar. Zendaya wore a brown plaid skirt that completely clashed with her red jersey-inspired long-sleeve top emblazoned with the number 39. Meanwhile, every element of Tom Holland's outfit was a different color. His beige jacket on top of a plaid light blue button-down gave American West vibes on the British actor. Their vintage style references did not go unnoticed by the internet. "They look like they are going down to the diner for a milk shake," one Redditor said. 

Despite being the man of the hour at the Los Angeles premiere of "Spider-Man: Brand New Day" at Dolby Theatre on July 27, 2026, Tom Holland's wardrobe did not seem carefully thought out. While he was possibly getting a bit bored with wearing his famous Spider-Man suit by then, his maroon suit with a bright red shirt underneath did not bring forth a brand-new day in fashion. He completed the look with a navy-blue tie that recreated the color palette for his onscreen character. Unfortunately, the suit itself was loose and ill-fitting on the star. While Zendaya was dressed to the nines beside him, her pointy all-black ensemble and styling made her look more like the movie's villain rather than the hero's love interest. Some Redditors even said she was giving Venom or funeral vibes with her ensemble. 

Soon after their relationship was publicly confirmed in July 2021, Tom Holland and Zendaya attended the SiriusXM's Town Hall together along with the rest of their "Spider-Man: No Way Home" castmates in December 2021. They both had made questionable outfit choices, from Zendaya's Pepto-Bismol pink suit to Holland's button-down shirt that looked like TV static. Holland's shirt paired with jet black pants was dull and unflattering on the actor. While it is hard to make Zendaya look bad, the solid-colored suit was a surprisingly unflattering choice for the A-list actor.

When Zendaya and Tom Holland attended the photocall for "Spider-Man: No Way Home" in London in December 2021, they appeared to have both been wronged by the same jacket salesman. Zendaya's gray coat looked several sizes too large to compensate for her lack of pants, ultimately swallowing her frame in a box-looking fit. Meanwhile, Holland's black leather jacket looked too short, as it appeared to stop well before his waistline. While Zendaya's spider-themed attire was appropriate for the occasion with intricate bejeweled tights and spiderweb earrings, what could have been a stunning and on-theme look was sabotaged by the lack of a tailor. 

Despite when Tom Holland and Zendaya's relationship really began, that did not stop them from igniting romance rumors in 2017. On June 15, 2017, they arrived together at the "Spider-Man: Homecoming" photocall at The Ham Yard Hotel in London. Zendaya's outfit attracted all the attention, both good and bad, alongside Holland's bland black shirt and jeans combo that seemed more appropriate for a movie theater date than a promotional event for his own movie. Zendaya wore a layered blue skirt paired with a black and yellow long-sleeve sweater that would have been more appropriate for promoting the "Bee Movie" instead of a movie about spiders. The short skirt and long shirt looked messy because their colors and styles clashed so much. 

Just three days after their fashion flop in London, the pair suffered a consecutive fashion flop at the CineEurope event in Barcelona on June 18, 2017. Tom Holland was once again underdressed, this time sporting black jeans instead of blue. He remained in the same black boots as the prior event and wore another black button-down. At least his shirt was patterned, and he elevated the look with a black leather jacket, which was an overall fashion improvement. Meanwhile, Zendaya continued to suffer from an overuse of colors that clashed. It also appears she may have joined Holland in recycling the same shoes from the past event. 

While it can be cost-effective and good for the environment to re-wear the same clothes, actor Tom Holland may have taken it a step too far in 2017. For his third worst fashion flop that occurred in the year of 2017, he once again wore the same black boots. When he and Zendaya got on stage together for the MTV Movie and TV Awards in May 2017, he was sporting his favorite kicks with a forgettable dark ensemble, while while Zendaya wore a puke-green gown that was sheer around her legs. With the footwear making an appearance in so many of the budding couple's fashion mishaps in 2017, it makes you wonder if perhaps Holland simply did not own any other shoes that year. 

2017 proved to be the couple's most trying year in fashion, especially during the June promotions of "Spider-Man: Homecoming." While promoting their first film together, they attended a photo call at the Whitby Hotel on June 25, 2017, in New York City alongside their other castmates. During this photo call, Zendaya wore a long-sleeve orange, yellow, and white striped dress that looked like candy corn. While the dress was an odd fashion choice in and of itself, she also wore it over a top with ruffled sleeves featuring a blue and purple floral print. The sleeves made no sense when paired with the dress, which had a totally different color palette. Meanwhile, Tom Holland continued his pattern of playing it safe with (almost) all-black ensembles.

Given the timeline of Zendaya and Tom Holland's relationship, they were not an official couple when they attended San Diego Comic-Con to join their costars at the Marvel Studios presentation in July 2016. However, the pair was already proving that they could both act and fashion fail together. Prior to their romantic relationship, Holland was already falling into the fashion trap of dressing in all-black ensembles when stepping out with his more sartorially adventurous co-star. Zendaya wore a gray dress with a splash of colorful florals that did not seem to fit the occasion, paired with black accessories that mixed neutral colors in an unflattering fashion.