Kylie Jenner sports slinky vintage Alaïa dress worth $30K with Timothée Chalamet

On Tuesday night, Kylie Jenner supported her boyfriend, Timothée Chalamet, at the Santa Barbara International Film Festival. kyliejenner/Instagram

Kylie Jenner brought the drama to the Santa Barbara International Film Festival.

The entrepreneur, 27, supported her beau Timothée Chalamet, 29, at the event on Tuesday night in a slinky vintage black dress.

Jenner, along with stylists Mackenzie Grandquist and Alexandra Rose, sourced the low-back halter gown from Azzedine Alaïa’s spring 1998 collection — which debuted on the runway the same year the social media star was born.

She stunned in a slinky vintage little black dress. kyliejenner/Instagram The number was sourced from Azzedine Alaïa’s spring 1998 collection — which debuted on the runway the same year she was born. kyliejenner/Instagram

The curve-hugging look is also extra pricey; it retails for a staggering $30,000 on luxury resale site 1stdibs.

The Kylie Cosmetics didn’t disappoint in the jewelry department on Tuesday night, either.

She accessorized with two gigantic diamond rings from Lorraine Schwartz, wearing an emerald-cut sparkler on her pointer finger and an oval diamond on her pinky.

Jenner upped the ante with statement diamond studs and coordinating silver earrings.

On Tuesday night, Jenner accessorized with two chunky diamond rings. kyliejenner/Instagram Chalamet, for his part, made a bold statement in a bright floral button-down. Getty Images for Santa Barbara International Film Festival Jenner was pictured in the crowd cheering him on. Rob Latour/Shutterstock

The Sprinter founder seems to be favoring vintage Alaïa dresses lately.

Last month, for example, she wore a see-through leopard minidress from its 1991 collection during Paris Haute Couture Week.

Jenner may have been influenced by her older sister Kim, who first rocked the designer’s leopard catsuit version in 2019.

Last month, Jenner wore a see-through leopard dress, which came from the designer’s 1991 collection. Instagram/kyliejenner Her older sister Kim first rocked Azzedine Alaïa’s leopard catsuit version in 2019. Instagram/kyliejenner

As for Chalamet at the awards show, he chose a punchier look, making a bold statement in a colorful Prada floral button-down shirt in green and yellow.

He layered the top over a tank in a complementing lime green hue, finishing the outfit with baggy True Religion bootcut jeans and white Bape sneakers. He added a diamond choker necklace, too, for some bling.

Per usual, Chalamet hit the red carpet solo and met up with the beauty mogul inside the event.

A video on X (formerly Twitter) caught Jenner rubbing her boyfriend’s back before he was announced as the recipient of the Arlington Artist of the Year Award for his performance in “A Complete Unknown.”

Last month, the couple attended the Golden Globes 2025. Penske Media via Getty Images Jenner skipped the red carpet and met up with her beau inside the event. Penske Media via Getty Images

Though they tend to keep their relationship relatively private, Jenner and Chalamet have been spotted together a few times this year.

The couple, who were first romantically linked in April 2023, made a rare public appearance at the Golden Globes 2025 on Jan. 5, where Jenner sparkled in a vintage Versace dress with a dangerously low back.

A few weeks later, Jenner supported Chalamet after his SNL hosting gig, meeting up with him at the afterparty, where they were later pictured sneaking out together.

We can’t wait to see what the reality star pulls out for the Oscars next month.