Zendaya Oozes '90s Nostalgia in Silver Jewelry, a Shoulder Bag, and 27-Year-Old Prada Boots

For Zendaya in L.A., Tank Top Season remains in full swing. That's not to say the street style looks in her September closet are leftovers from July. On September 17, Zendaya's black skirt and tall Prada boots gave her summer tank top a moody, autumnal twist.

Days after Z's custom Prada gown stole the show at the 2026 Emmys, she sourced the Italian label for an off-duty outfit. The Prada Beauty ambassador (a role she shares with her husband, Tom Holland) visited an art gallery in L.A., wearing a black one-shoulder tank. Over the summer, she wore a similar ribbed style—whether it was black, brown, or white—for the rare occasions when she wasn't promoting Spider-Man: Brand New Day or The Odyssey.

This time around, she included the tank in a fall outfit that's perfect for those 65-degree, "I don't have anything to wear" days. The Emmy winner wore a navy knee-length skirt and black moto boots, both from Prada. Not only was the midi woven from thick, December-worthy wool (a bold move for an L.A. look), but oversized buttons and cinched paneling created an almost bubbled silhouette. Her exact style is sold out, but if you're lucky, it'll pop up on secondhand sites. The same skirt recently sold at Vestiaire Collective for nearly $1,000.

Now, onto her boots. Sadly, the padded calf-length pair is just as tricky to track down as her skirt. Turns out, the Linea Rossa Boots are a rare circa-1999 design from Prada Sport, the athleisure label that the fashion house launched in the late ‘90s.

Despite being 27 years old and the product of a defunct brand, all hope for securing the lug-sole style isn't lost. In addition to Zendaya, Bella Hadid and FKA Twigs own the same boots. Three years ago, Hadid debuted them beneath a trench coat, a black turtleneck, and matching trousers. While the supermodel's pants shielded both shafts, the signature arched soles confirmed they were the Linea Rossa style. Meanwhile, as recently as March 2026, FKA Twigs wore the leather boots while performing in Miami.

As for Zendaya's accessories, she kept it simple, styling silver button earring studs with her Jessica McCormack engagement ring and a cut-out shoulder bag by Ferragamo. The entire look exuded '90s nostalgia, but not just because of her vintage scores. The Euphoria actor's Halle Berry-esque haircut played a major part in the throwback, too.

Here we have another classic "sisterhood of the traveling vintage" case. But Zendaya is no stranger to a hand-me-down moment in Hollywood. After all, she wore Sarah Jessica Parker's Sex and the City dress at the 2026 Essence Black Women in Hollywood Event and Cate Blanchett's Armani Privé gown at The Drama premiere in Rome.

Setting the vintage finds aside, Zendaya's latest look is a master class in summer-to-fall styling. To follow her lead, shop the non-archival attire below.

Shop Summer-to-Fall Outfits Inspired by Zendaya