Kylie Jenner and Timothée Chalamet Tease a 2026 Met Gala Debut With Their Latest Date Outfits

Kylie Jenner has walked the Met Gala red carpet alone for the last seven years. But boyfriend Timothée Chalamet wouldn't leave his girl hanging, would he? On the eve of the 2026 Met Gala, Jenner and Chalamet were hand-in-hand steps away from New York City's most iconic staircase. Fingers crossed this means they'll make their Met Gala couple debut later tonight.

Jenner and Chalamet joined Kim Kardashian at the May 3 performance of Broadway's Fear of 13—the Adrian Brody and Tessa Thompson-led play Kardashian helped produce. The power couple wasn't nearly as dressed up as Kardashian, who arrived in archival Dior by John Galliano. But they were the coolest couple in the James Earl Jones Theatre, no questions asked. Jenner wore all-black basics as her base layer, including a skintight take on the capri pants trend. Her capris matched the Spring 2026 shoe trend she rarely takes off: heeled flip-flops.

Each leather, V-shaped strap and two-inch heel looked fresh from its Manolo Blahnik box, despite being in regular rotation since 2024. Jenner wore the Paterno Sandals as recently as last week's New York Knicks game, alongside vintage white jeans from Isabel Marant and a matching crop top. Last night, however, Jenner's flip-flops outfit took cues from her sister's minimalist closet instead.

Kylie's Broadway-ready outerwear felt so on-brand for the oldest Jenner sister, Kendall. (Meanwhile, Kylie is usually seen in sportier track jackets and bombers, all worthy of spots in her boyfriend's closet.) Kendall's coat rack is stocked with similar, camel-colored trenches. Last March, her double-buckled version matched the length and slightly-oversize silhouette of Kylie's. She styled it with cigarette jeans and a Hermès Kelly bag, though. The only thing the Khy founder carried was Chalamet's hand.

Back to Chalamet: The fashion guy kept it casual in a (still shoppable) track jacket from Adidas, baggy black joggers, and stark white sneakers. But Chalamet will match his girlfriend's designer energy if the right red carpet rolls around. For instance, the Dune actor rarely attended an award show this year without Jenner close by. The couple didn't always grace the red carpet, but they'd pose for mid-ceremony photographers with just as much finesse.

Jenner and Chalamet started their award season sweep at the 2026 Critics Choice Awards, where Jenner's vintage chainmail dress from Versace Fall 1996 felt just as nostalgic as Chalamet's pinstripe Givenchy suit.

Later that week, the two were all smiles once Chalamet won Best Actor in a Motion Picture—Musical or Comedy for Marty Supreme at the 2026 Golden Globes. But who needs a trophy when Jenner is your date? She traded archival for a custom Ashi Studio bustier gown, crafted from metallic, brushed gold sequins.

It wasn't until last month's 2026 Vanity Fair Oscar Party that Jenner and Chalamet walked an actual award show red carpet together. Sorry, Chalamet, but Jenner stole the show in a handcrafted McQueen gown, featuring a plunge halter neckline, a partial hip cut-out, and black feathers atop the carpet-grazing train. Chalamet was the ultimate blank canvas behind her, in a white Chrome Hearts suit.

Only Jenner and Chalamet know for sure if they're making their Met Gala couple debut tonight. But all signs point toward RSVPs from not one, but both VIPs. While you await their outfit reveals, busy yourself by shopping the Jenner-inspired edit below.

Shop Date Night Styles Inspired by Kylie Jenner