When Kylie Jenner showed up solo at the 2025 Met Gala red carpet in custom Ferragamo, it seemed the hopes of a red carpet debut with boyfriend Timothée Chalamet were squashed. Actually, the duo just wanted to wait for another event to finally take on the cameras together—and in matching outfits, at that.
Kylie Jenner and Timothée Chalamet jetted to Rome, Italy, for a romantic stroll down the 70th David Di Donatello Awards at Cinecitta Studios red carpet. The pair could have been dressed for the opulent gala Chalamet skipped back in New York City. He looked debonair in a black velvet tuxedo by Tom Ford, set with a white rosette pin, while Jenner glistened by his side in a plunging Schiaparelli gown. While the event is billed as the Italian equivalent of the annual Academy Awards, the pair treated it more like date night. Jenner and Chalamet held hands all the way down the carpet, pausing for a half-hug in front of the cameras.
Jenner appeared to put her years of attending Schiaparelli fashion shows to good use for her red carpet hard-launch with Chalamet. She and her stylists, Mackenzie and Alexandra Grandquist, pulled her sculpted gown from Schiaparelli's Fall 2025 runway. Just like the original presentation, she styled the gown with oversize, mismatched gold and pearl earrings and concealed her heels (also by Schiaparelli) beneath the floor-grazing skirt. For an extra date night touch, Jenner added a sculptural velvet clutch, set with the house's signature keyhole motif.
Kylie Jenner and Timothée Chalamet started dating back in 2023, but the pair didn't really join fashion forces until Chalamet's Academy Award campaign last year. Once the actor started racking up nominations for portraying Bob Dylan in A Complete Unknown, he would often invite Jenner as his plus-one to international film festivals and award ceremonies.
The pair saved their red carpet debut for this May, but they still planned their outfits for inevitable photos inside each event. Jenner picked out a vintage gown worn by Elizabeth Hurley to sit at Chalamet's table during the 2025 Golden Globes. At the Oscars, she snuck into the ceremony in custom Miu Miu before hitting the after party wearing a corseted dress by Ashi Studio. Cheering on Chalamet has also involved a slew of beaded, backless vintage dresses by John Galliano.
Chalamet and Jenner tipped off fans to their couples' style ambitions just last week, when they sat courtside at an LA Lakers game. Jenner wore vintage Roberto Cavalli and a $54,000 Cartier watch, while Chalamet chose a Chanel jacket and vintage tee. Between their red carpet debut and their casual hangs, this much is true: They're a couple with opulent taste.
