Zendaya Flexes Her Rare Vintage T-Shirt in Boyish Baggy Trousers and White Sneakers

Zendaya never slacks when it comes to her street style. On Thursday, Oct. 17, the Euphoria star stepped out in Los Angeles wearing a casual outfit that still showed off her fashion prowess.

The standout piece was a rare vintage T-shirt featuring a print of artist Gilbert Young's painting, "He Ain't Heavy." The shirt has been in Zendaya's closet since 2017 at least and the garment is thought to be an homage to her KC Undercover co-star Kadeem Hardison. Hardison once wore an identical shirt on the '80s sitcom A Different World, in which the actor famously played a lovable nerd named Dwayne Wayne. The shirt has since become nearly impossible to find—but I did manage to locate one going for $200 on Depop.

Graphic tees like Zendaya's are making a major comeback this year, thanks to Gen Z's obsession with Y2K and indie sleaze aesthetics. Recently, lovebirds Gracie Abrams and Paul Mescal coupled up in coordinating vintage T-shirts for an outing in New York City. Elsewhere, a slew of celebrities including Charli XCX and Zoë Kravitz have been spotted in Stella McCartney's "About F–cking Time!" tank top, which dropped in the designer's Fall 2024 collection. Kaia Gerber also embraced the trend in graphic tees from her reading group, Library Science, over the summer.

Alongside Zendaya's fresh fall manicure, the 28-year-old actor paired her vintage twist on the trend with baggy brown pleated trousers, blue socks, and white On Running sneakers inspired by tennis icon Roger Federer. Zendaya became a brand ambassador for the Swiss footwear brand in June following her portrayal of Tashi Duncan—a former tennis prodigy turned coach—in director Luca Guadagnino's steamy sports thriller Challengers. Earlier this week, she gave the brand another nod by pairing its biker shorts with a pair of Ugg slippers.

The rest of her look was largely un-accessorized apart from stud earrings, a gold cuff bracelet, and a delicate gold chain necklace. Her honey-blonde hair—which she's been gradually lightening since late March—was pulled into a messy low bun. Her skin, meanwhile, seemed mostly makeup-free. I suppose that's just another perk of being Miss Z: No matter how much she dresses down, she always looks picture-perfect.