Wait. Did she actually just do that?
For years, the biggest question surrounding Hollywood’s biggest night wasn't who would take home the gold statue, but rather: where on earth is Kylie? We've seen her dominate the Met Gala. We’ve seen her own the front row in Paris. But the Academy Awards? That was always the one fort she hadn't quite stormed.
Then 2025 happened.
Kylie Jenner at the Oscars was no longer a "maybe" or a "she’ll show up to the after-party." She was actually in the building. Inside the Dolby Theatre. Sitting right there in the front row. And honestly? The way she pulled it off was kind of a masterclass in staying low-key while being the most talked-about person in the room.
The Secret Entry Strategy
Most stars spend three hours bake-heating under the California sun on the red carpet. Not Kylie. She basically pulled a ninja move. She skipped the official red carpet entirely, avoiding the "who are you wearing" shout-fests, and slipped into her seat next to Timothée Chalamet while the lights were low.
It was a bold move.
She was there to support Timothée, who was nominated for Best Actor for his role as Bob Dylan in A Complete Unknown. Because she skipped the carpet, the world didn't even know she was there until the camera panned to Chalamet and caught her looking like a literal dream in custom Miu Miu.
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It wasn't just about the boyfriend, though. There was a deeper, much sadder layer to her appearance that night. Just a week before the ceremony, Kylie lost her longtime friend and hairstylist, Jesus Guerrero. Her makeup artist, Ariel Tejada, shared on Instagram how "hard" the glam process was without him.
They did it for Jesus.
You could feel that weight in the look. It wasn't just a "pretty dress" moment; it felt like a tribute.
Breaking Down the Miu Miu "Lingerie" Moment
Let's talk about the first dress because it was... a lot. In the best way possible.
The custom Miu Miu gown was basically a study in contrasts. You had this heavily beaded black push-up bra bodice that looked like high-fashion lingerie, which then transitioned into an ultra-high-waisted silk column skirt. It was edgy. It was "Kylie."
- The Details: Beaded cut-outs, Lorraine Schwartz diamonds, and a deep side-part blowout.
- The Vibe: Understated but incredibly expensive.
- The PDA: Yes, they were caught whispering and kissing. It was the "hard launch" the Oscars didn't know they needed.
Timothée, for his part, looked like a literal stick of butter. He wore a yellow leather suit by Sarah Burton for Givenchy. Somehow, sitting next to each other, the black and yellow combo worked. It shouldn't have, but it did.
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The Vanity Fair Switch-Up
You can't talk about Kylie Jenner at the Oscars without discussing the after-party. That’s her home turf.
Once the ceremony ended and the pressure of the nomination was off (Timothée lost to Adrien Brody, by the way), the couple headed to the Wallis Annenberg Center for the Performing Arts. This is where Kylie 2.0 emerged.
She swapped the Miu Miu for a sheer lace corset dress by Ashi Studio. This look was "naked fashion" at its peak. It featured a black lace pattern over a nude underlay, creating the illusion of transparency while staying perfectly tailored.
Honestly, it was more daring than the ceremony dress.
While she skipped the Vanity Fair red carpet too—preferring to meet Timothée inside—the photographers caught them looking completely inseparable. At one point, she was seen pressing her cheek against his while he beamed. It’s clear she wasn’t just there for the fashion; she was there for him.
A History of After-Party Domination
To understand why this was such a big deal, you have to look back at her track record. Kylie has been a Vanity Fair Oscar Party staple for years, even when she had no reason to be at the actual awards.
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- 2020: She wore that famous navy Ralph & Russo gown that was so tight she literally couldn't sit down. She posted videos of herself reclining in a van because the sequins were like armor.
- 2023: She did a custom metallic Maison Margiela moment that felt very "Schiaparelli-adjacent."
- 2024: She wore burgundy chainmail by Ludovic de Saint Sernin.
But 2025 was different. It was the first time she was a guest at the actual ceremony. It felt like an evolution from "reality star at the party" to "partner of a Hollywood heavyweight."
What This Means for the "Kylie Era"
People have been obsessed with how Kylie’s style has changed since she started dating Chalamet. Some call it the "clean girl" transition. Others say she's just growing up.
When asked by The New York Times if his influence changed her wardrobe, she was pretty coy. She basically said she didn't want to talk about personal things. Fair. But you can't deny the shift. The clothes are more archival, more "custom couture," and slightly less "Instagram baddie."
The Oscars appearance solidified this. She chose designers like Miu Miu and Ashi Studio—brands that command respect in the high-fashion world—rather than just wearing what’s trending on TikTok.
Actionable Takeaways for Fashion Lovers
If you’re looking to channel the Kylie Jenner Oscar energy without a billionaire's budget, there are a few "formula" secrets to steal from her 2025 appearance:
- The "Lingerie" Rule: Mixing boudoir elements (corsets, lace, bra-tops) with structured silhouettes (long skirts, blazers) makes the look feel "red carpet" rather than "night out."
- Skip the Necklace: Notice she rarely wears heavy necklaces with busy necklines. She lets the dress do the talking and sticks to statement rings or earrings.
- The "No-Red-Carpet" Red Carpet: You don't always have to be the first one there. Sometimes, the most impact comes from a well-timed "entrance" inside the event.
Kylie’s journey to the Oscars was a long time coming. Whether you're a fan of the relationship or just the clothes, there's no denying she knows how to handle a spotlight—even when she's trying to stay out of it.
To keep up with her latest style shifts, you can follow her stylists Alexandra and Mackenzie Grandquist, who have been the architects behind this "High Fashion Kylie" era. Watching the archives of designers like Ashi Studio can also give you a head start on the "naked dress" trends that will inevitably hit the mainstream next season.