If you were hoping for another Kylie Jenner Oscars sighting, this one’s for you. Though she kept with tradition and opted *not* to walk the red carpet at one of boyfriend Timothée Chalamet’s events, the reality TV star made an appearance during the first few minutes of the awards ceremony’s live broadcast. And her dress was nothing short of jaw-dropping.
Kylie’s Cherry-Red Gown
During a few blink-and-you’ll-miss-it moments at the top of the 2026 Academy Awards, Jenner could be seen wearing a figure-hugging halter gown crafted in a glittery red fabric that would give Jessica Rabbit a run for her money. Not so coincidentally, the Kylie Cosmetics founder captioned a video of her look on Instagram, “Jessica who?”
Jenner’s stunning attire, designed by Daniel Roseberry for Schiaparelli, featured a décolletage-forward neckline with the label’s signature keyhole cutout. She paired the already-glitzy number with even more sparkle — 200 carats worth, to be exact. The dazzling accessories included a Lorraine Schwartz diamond necklace with two massive teardrop pendants, as well as equally frosted earrings and a huge ring.
If the gown looks familiar, that’s because she wore a version in a different color in 2023 when she attended Schiaparelli’s Paris Fashion Week Spring/Summer 2024 show. Talking about the ‘fit with Vogue, Jenner called it her “favorite look of all time.”
“It was just perfect. I definitely felt the most beautiful I’ve ever felt in my life,” she added. “I think it was one of the first times he ever showed the keyhole.”
After raving about Roseberry’s vision, she added, “Anytime I’m trying to figure out what to wear for an event, I’m like, ‘Should I just wear the keyhole dress again?’ I think I need another moment in this dress. Or maybe another color.”
Her After-Party Attire
Later that night, Jenner accompanied Chalamet to the star-studded Vanity Fair after-party, where they finally walked the carpet together. Naturally, she changed into a second look to commemorate the moment: a custom Alexander McQueen.
Thanks to the ornate beading, the fit-and-flare halter number glistened with every move. It featured a deep V-neckline and an asymmetrical hip cutout on one side, as well as small fabric embellishments made to resemble a heap of feathers, one of spring’s biggest fashion trends.
In contrast, Chalamet wore his second all-white look of the night, albeit with a more casual, relaxed fit.
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