Occasions When Zendaya Nearly Made the Worst-Dressed List

Zendaya shared another fashion choice she regretted with Oprah.com, admitting she was no fan of the ruffled, floral, button-up dress she wore to the “Gnomeo and Juliette” premiere in 2011. She paired the youthful, layered skirt garment with brown, wingtip-esque block heel boots, which aged up what could otherwise have been a cute look for the young teen. 

“It wasn’t very flattering — I hadn’t gotten that far in my style evolution yet. I was 13 at the time, but still,” Zendaya said. Though we’ve seen worse fashion disasters, Zendaya admitting she didn’t feel comfortable in the ‘fit automatically qualifies it for the worst-dressed list.

In 2014, Zendaya attended the Teen Vogue Young Hollywood Party in a black jumpsuit. She attempted to make the monochrome look interesting by adding a seriously oversized bowler hat, which was even bigger than her head. Though we appreciated the risky attempt to elevate what could have otherwise been a boring outfit, the avant-garde hat was too distracting.

A Teen Vogue party is also place to let fun, youthful fashion dominate, and the dark, matte look felt too serious. Although Zendaya said she loves the look to this day, she admitted the reaction was mixed, joking to Elle, “People were like, ‘Oh no, Zendaya’s gonna start looking like this now.'”

Sometimes, even the most gorgeous (and tall) of us can’t pull off an unflattering skirt. Zendaya attended a 2013 pre-Grammy event in a Snow White graphic T-shirt, leather-look jacket, pink heels, and metallic tulip skirt with barely-there floral detailing. But the execution wasn’t on point. 

The attention-grabbing skirt was too long and would have looked chicer if it sat slightly higher on her waist. It also needed to be rotated so the slit fell over her left leg. Her T-shirt didn’t work either, as it felt too casual and slouchy for a red carpet. We’d have recommended she swap to a black, sleeveless bodysuit to let the skirt be center of attention.