Kylie Jenner
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Fashion

10 Looks We’d Love To See Kylie Jenner Wear This Awards Season

In the words of Tyla, “Say you love me, put me in Chanel.”

by Kevin LeBlanc

Fact: Kylie Jenner is the most famous plus-one at any awards-season event she’s been to this year. Her three-year relationship with Timothée Chalamet has been largely under wraps, but in his last two acceptance speeches, he called out his “partner” and gave her her flowers. Another fact: She’s shown up to each event as under-the-radar as possible, often skipping the media frenzy that is the red carpet. They have only walked a handful of carpets together, the most recent (and memorable) of which was their matching orange moment at the Marty Supreme premiere in Los Angeles. She’s been with him every step of the way (if only inside the ceremony) in custom, vintage, and otherwise wow-factor gowns.

We love her style and her stylists — we named the Grandquist sisters one of our stylists to watch last year — and don’t think we can do their jobs for them by any means, but we can’t help but make a wishlist of our own for the remaining appearances we assume she will make alongside Chalamet at, say, The Actor Awards, the BAFTAs, and yes, the Oscars. Jenner has the world at her fingertips when it comes to fashion, and we put together a list of designer gowns, from the most global names to emerging start-ups we love, that we’d love to (selfishly) see her wear. Keep reading to see what dresses King Kylie would no doubt turn heads in below.

Schiaparelli

Schiaparelli Spring/Summer 2026Courtesy of Schiaparelli

This is in line with her body-con taste, but with a high-fashion update. Plus, the hip tear-aways speak to her curvy figure.

Francesco Murano

Francesco Murano Spring/Summer 2026Estrop/Getty Images Entertainment/Getty Images

This fits Kylie’s body-skimming checklist, but the top gives more coverage in a refreshing way. Francesco Murano is also a star on the rise.

Chanel

Chanel Metiers d’Art 2026Copyright CHANEL

Classic Old Hollywood glamour, in a color we rarely see Kylie in. This would be a fabulous dress to pair stunning jewels with, too.

Balenciaga

Balenciaga Summer 2026Victor VIRGILE/Gamma-Rapho/Getty Images

A more demure Kylie that feels equal parts gothic and high camp. We don’t see her wearing this with flip-flops, of course, but we’re into the bolero leather moment paired with a dramatic skirt, something she hasn’t worn in a while.

Colleen Allen

Colleen Allen Spring/Summer 2026Courtesy of Colleen Allen

Colleen Allen is behind some of our favorite looks on people like Greta Lee and Emma Stone, and this simple jersey dress would kill on Kylie — just add a backwards necklace and you’re off to the races.

Courrèges

Courrèges Spring/Summer 2026Courtesy of Courrèges

White isn’t a color she leans towards, but this geometric, sensuous dress from Courrèges would be an ideal dress for King Kylie’s tan and amazing hair.

Armani Privé

Armani Privé Fall 2025 CoutureVictor VIRGILE/Gamma-Rapho/Getty Images

If Cruella de Vil and Morticia Addams had a baby, it would be Kylie in this look. This is relatively simple — save, of course, the opulent horizontal feather piece.

Erik Charlotte

Erik CharlotteInstagram/@erikch4r

Our favorite lady of fantasy, Erik Charlotte, is known for her opulent, taffeta-heavy creations, but this pared-back linen-and-silk gown would be a departure for Kylie in the best way possible. Not only would it show off her covetable body, it would show her love for emerging designers and hand-sewn corsetry.

Trochopoulos

Trochopoulos Spring/Summer 2026Instagram/@trochopoulos

Georg Trochopoulos’ brand, Trochopoulos, is a master of knits, and this delicately embroidered moment would serve Kylie well for a more casual gathering as Timothée’s plus-one.

Loewe

Loewe Pre-Fall 2026Instagram/@loewe

Jack McCullough and Lazaro Hernandez have been busy at work reimagining Loewe in their color-soaked, minimalist lens, and this Pre-Fall dress paying homage to former Loewe creative director Narciso Rodriguez is the dose of primary-color beauty Jenner’s beauty would complement beauitfully.