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

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.

Jenner once told us her mom is her style icon, so it makes sense they would pair up on the red carpet, too. Here, the star wore a Cushnie et Ochs top with Alaïa leggings and a Kimora Lee Simmons coat to the premiere of The Gallows.

Wearing Balmain x H&M, Jenner appeared at the launch of the brand’s capsule collection in 2015.

Completing the arc that brought her into Olivier Rousteing’s fold, Jenner wore Balmain to the 2015 Billboard Music Awards.

This cutout Steven Khalil gown was Jenner’s outfit of choice for the 2015 GQ Grammys afterparty.

Jenner matched her black bob to this silk Alexandre Vauthier number and patent Gucci heels at the 2014 MTV Video Music Awards.

Jenner once again chose Alexandre Vauthier, this time in burgundy, for the American Music Awards.

Jenner opted for an orange Nicolas Jebran mini dress at the MuchMusic Video Awards in 2014.

The blue dye of Jenner’s bob popped against the white palette of her Alex Perry dress and Louboutin heels during the 2014 Billboard Music Awards.

Kylie, in Maiyet and Giambattista Valli, debuted a new hairstyle when she walked the red carpet at the American Music Awards with her sister Kendall.

The star went with a sleek black two-piece look to attend the premiere of After Earth (the movie fronted by then-boyfriend Jaden Smith) in 2013.

The mogul opted for white and nude, a palette she’d come to favor down the line, at the 2013 MTV Movie Awards.

Jenner wore a dress by Msfts, the label designed by her then-reported boyfriend, Jaden Smith, to the Kids’ Choice Awards in 2013.

Kylie Jenner packed on the sparkle for Fashion’s Night Out in 2012.

In coordinating blue dresses, Kendall and Kylie proved their twinning days were just getting started in 2011.

Though Kylie opted for a white strapless dress, she seemed to match her nude patent heels to Kendall’s Louboutin pair for the premiere of Justin Bieber: Never Say Never.

Kylie wore a floral minidress at the 2009 release party for Selena Gomez’s album Kiss and Tell.

Kendall and Kendall joined momager Kris at a 2009 KIIS-FM event.

A pre-teen Kylie Jenner attended a 2008 charity event in white shorts and a ruffled blouse.

The Jenner family looked as stylish as ever (was this Kylie and Kendall’s first matching moment?) at the world premiere of The Emperor’s New Groove in 2000.