Zendaya gave us Old Hollywood glamour at the 2025 Golden Globes, then turned around and gave us a different flavor of classic style at a special Challengers screening with director Luca Guadagnino the very next day. On Sunday, Zendaya wore a burnt orange gown with a retro curled bob. On Monday, her hair was back to black and styled in a high ponytail, worn with biker-chick-inspired black leather.
Zendaya’s look for the screening combined a black leather blazer, buttoned and tightly fitted, with a flouncy black tulle miniskirt, as if Z was a ballerina with a Harley. The black jacket looks to be from John Galliano’s Dior fall 2003 ready-to-wear collection, in keeping with the vintage theme of the past couple of days.
Her high ponytail was extra dramatic thanks to curtain bangs and long, face-framing layers on either side. And with hair this big, there’s no need for much jewelry, so Zendaya skipped the necklace and opted for understated stud earrings.
There was one consistent accessory between both Zendaya’s Golden Globes look and her screening ’fit, however, and that was her new engagement ring.
Fans watching the Golden Globes were quick to clock that Zendaya appeared to be wearing a large diamond ring on that finger, and that the diamond didn’t match her other Bulgari jewelry. Soon, TMZ and People had both confirmed that Zendaya and her longtime boyfriend, Tom Holland, had gotten engaged over the holidays. The Globes were Zendaya’s first public appearance wearing the ring, and the screening in Los Angeles was the second. The ring itself is not vintage but is rumored to be by celebrity-favorite jewelry designer Jessica McCormack—one of her signature designs, described as “the perfect modern engagement ring…beloved by cool brides for its pared-back, non-traditional aesthetic.”
Vintage or modern, we can always count on Zendaya to look cool.
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