Kylie Jenner’s Signature Red Carpet Style Has Come a Long Way

Kylie Jenner is a woman of superlatives, or at least of notable firsts: She’s the youngest Kardashian; she’s allegedly a self-made billionaire; she’s the sister who has undergone the most radical style transformation. Not bad for a Gen Z-er with four accomplished older sisters and an Olympian for a parent. She was born into a reality-television dynasty, and as a result, grew up in the spotlight, accompanying her parents on the red carpet and frequently twinning with her older sister, Kendall Jenner.

But over time, Kylie has cultivated a look that sets her apart from her closest sibling and places her in a lane of singular statement-making. In recent years, she’s established relationships with some of the biggest brands and designers—from Jean Paul Gaultier and Maison Margiela to Mugler and Schiaparelli. She’s embraced Kardashian-esque bodycon, while serving supermodel-worthy surrealism. And despite having started in the world of beauty products with Kylie Cosmetics, she’s also tried her own hand at fashion design, with the release of her clothing label Khy. The 29-year-old’s love affair with fashion is certainly not hard to see. Below, W breaks down her red carpet evolution—from tween star and reality-show daughter to designer muse and self-described “cool mom.”

To honor the “Costume Art” theme, Jenner played with the image of being undone in an otherworldly Schiaparelli corset gown designed to look as though it was slipping off her hips.

Jenner had a short but impactful cameo in Charli xcx’s mockumentary The Moment. To celebrate her foray into the acting world, the star wore an appropriately theatrical ensemble—courtesy of Maison Margiela.

It was a couple-matching moment for the ages. In honor of Marty Supreme’s bright palette, Jenner stepped out in a custom Chrome Hearts cutout dress that complemented her boyfriend Timothée Chalamet’s three-piece orange suit. The look went viral and spoke to Jenner’s ability to have fun with fashion.

To mark a decade since her beauty brand’s inception, Jenner evoked King Kylie-era styling in a long pink wig and latex dress.

In May 2025, Kylie and Chalamet made their long-awaited red carpet debut. Jenner, of course, used the moment to make a low-key fashion statement—she wore a simple spaghetti strap dress from Schiaparelli and the label’s signature gold jewelry.

The model turned to Ferragamo’s Maximillian Davis at the 2025 Met Gala, wearing a sheer look with a daring skirt inspired by a tuxedo jacket.

Don’t get too close to the mogul’s Schiaparelli dress—it has spikes.

Jenner channeled Madonna’s infamous cone bra at the 2024 Met ball in a champagne hued look by Oscar de la Renta.

Jenner’s choice of Haider Ackermann for the 2023 Met Gala may have surprised some, but the red and blue cutout gown looked oh-so right on the event’s iconic red carpet.

Kylie wore a custom silver Maison Margiela bow dress and Amina Muaddi heels for the 2023 Vanity Fair Oscar Party.

The Khy designer turned heads in this roaring Schiaparelli velvet dress (featuring an extremely realistic 3D lion head) for the brand’s runway show during Paris Fashion Week.

For the opening of Thierry Mugler: Couturissime at the Brooklyn Museum, Kylie looked otherworldly in a black corseted gown and glittering headpiece.

Kylie looked as chic as ever in this one-shoulder and sheer Thierry Mugler dress for the 2022 CFDA Awards.

Clearly, she was feeling the lace look when she chose this lingerie-inspired Mugler ensemble to attend the Business of Fashion 500 Gala.

Jenner brought along her daughter Stormi to the 2022 Billboard Music Awards, where she wore a curve-hugging silver and navy Balmain dress.

Jenner chose a dramatic, bridal-style gown from Off-White (complete with a baseball cap veil) to attend the 2022 Met Gala.

The model looked ravishing in a green Jean Paul Gaultier cone-bra dress for the 2021 Parsons Awards.

Jenner opted for a glittery Ralph & Russo couture gown at the 2020 Vanity Fair Oscar Party.

She understood the assignment in a purple Atelier Versace gown for the 2019 Met Gala themed “Camp: Notes on Fashion.”

Wearing a sculptural pink Balmain couture outfit, Jenner certainly made a statement for the 2019 Grammy Awards.

Channeling businesswoman chic for the 2018 MTV Video Music Awards, Kylie wore a white suit dress and silver heels.

Jenner opted for a strapless Alexander Wang gown and sleek, crystal-encrusted sunglasses for the 2018 Met Gala.

Jenner and sister Kim Kardashian attend the Louis Vuitton Men's spring 2019 show in equally colorful looks.

For the 2017 Met Gala, Kylie Jenner showed up in a custom Versace dress that she styled with an edgy platinum bob.

Kylie Jenner quite literally shined in a custom La Bourjoisie gown at the 2017 Golden Globes.

Jenner called on Balmain’s then-creative director Olivier Rousteing to outfit her in this cutout sparkling gown for the 2016 Met Gala.

Glistening in gold, Shady Zeineldine, Jenner attended the 2015 ESPYS in Los Angeles, California.

A regular at the American Music Awards, the star went custom for the 2015 edition in a chainmail and leather Bryan Hearns number.