Kylie Jenner, Timothée Chalamet Pack on PDA at Vanity Fair Oscar Party

While the couple didn’t walk the red carpet together at the Conan O’Brien-hosted event, the Kylie Cosmetics founder—mom to daughter Stormi, 8, and son Aire, 4, with ex Travis Scott—showed off a separate Jessica Rabbit-inspired Oscars dress on social media before slipping inside the Dolby Theatre in Hollywood, Calif., to support her boyfriend.

Her first look of the night—a skin-tight Schiaparelli gown—was red-hot to say the least. Complete with a lock-shaped cut out on the chest and a deep-V halter neckline, the deep shimmery red dress was best-in-show. 

But their prize-worthy date night wouldn’t be complete without a few laughs. In fact, after Conan took a good-natured jab at the A Complete Unknown star for his controversial comments on ballet and opera, Timothée couldn’t help but giggle. 

"Security is extremely tight tonight," Conan jokingly told the crowd during his opening monologue. "I'm told there's concerns about attacks from both the opera and ballet communities."

The camera then panned to Timothée and Kylie who took the joke in stride as they could be seen laughing. 

Though Timothée didn’t take home the award for Best Actor—that honor went to Michael B. Jordan—he and Kylie undoubtedly had a winning date night. But it wouldn’t be their first night on the town during award season. After all, Kylie has been the Little Women actor’s plus-one to all the major ceremonies of 2026.

Though the pair is notoriously private about their relationship, Timothée even made his first public comments about his relationship when he won the Critics Choice Award for Best Actor.

“Lastly, I'll just say thank you to my partner of three years,” he said during the Jan. 4 ceremony. “Thank you for our foundation. I love you. I couldn't do this without you.”

For more stars on the 2026 Vanity Fair Oscars Party red carpet, read on…