Kylie Jenner Wore a Plunging Dress to the 2026 Oscars

Kylie Jenner and Timothée Chalamet on the red carpet for Marty Supreme premiere. — (Image credit: Getty Images)

Kylie Jenner has had a busy few months, and tonight, she's bringing that momentum straight to the 2026 Oscars red carpet. The beauty mogul and budding actress (Gen Z is raving about her cameo in Charli XCX's mockumentary, The Moment) arrived at the 98th annual Academy Awards in a plunging red Schiaparelli gown that felt equal parts glamour and classic Hollywood drama, instantly making her one of the evening's most talked-about attendees before she even arrived at the Dolby Theatre.

For her Oscars 2026 look, Jenner chose to channel another Hollywood icon—the fictional Jessica Rabbit—in a plunging, shimmery red gown from French fashion maison Schiaparelli and diamond jewelry from Lorraine Schwartz. The gown, a custom creation designed by Creative Director Daniel Roseberry, features a plunging neckline and a cool detail that makes the dress feel oh so 2026: a keyhole cutout below the bust.

While keyhole-cutout dresses have been trending on Hollywood red carpets since the '90s, Jenner's literal interpretation is silly and whimsical, something Roseberry has become known for.

See Kylie Jenner's Oscars 2026 Look

Kylie Jenner wearing a red Schiaparelli dress to the 2026 Oscars.

Jenner was styled by duo Mackenzie Grandquist and Alexandra Rose Grandquist. The Grandquists have lended their eye to Jenner's recent red carpet looks too—most notably the jaw-dropping hourglass look the 28-year-old wore while attending the Golden Globes 2026.

Jenner never shies away from a reason to turn a 'fit, but of course, there's another reason she's at the Academy Awards tonight: her boyfriend, Timothée Chalamet, who is nominated for Best Actor. The pair have been making their way through award season side by side, stepping out together across the red carpet circuit following the whirlwind press tour for Marty Supreme.

With Chalamet's category still ahead and the night just getting started, Jenner's dramatic Schiaparelli moment has set the tone for what's shaping up to be another major night for the couple. If this Oscars 2026 red carpet look is any indication, award season's most stylish duo isn't slowing down anytime soon.

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Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.