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

In May 2025, Kylie and her beau, Timothée 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 model’s Schiaparelli dress—it has spikes.

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

Kylie’s choice of Haider Ackerman for the 2023 Met Gala may have surprised some, but the red and blue cut-out 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 a lot of 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 the 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.

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

Kylie 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.

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

Kylie stole the show in a purple Atelier Versace gown for the 2019 Met Gala themed “Camp: Notes on Fashion.”

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

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

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

Kylie and Kim attend the Louis Vuitton Menswear spring/summer 2019 show in equally colorful looks.

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

When you’re a Kardashian, even the runway won’t do—Kylie went custom once again for the 2017 Golden Globes in a silver La Bourjoisie gown.

Kylie called on Balmain’s Olivier Rousteing to outfit her in this cut-out sparkling gown for the 2016 Met Gala.

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

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

Kylie once told us her mom is her style icon, so it makes sense they would pair up on the red carpet, too. Here, Kylie 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, Kylie appeared at the launch of the brand’s capsule collection in 2015.

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

This cut-out Steven Khalil gown was Kylie’s outfit of choice for the 2015 GQ Grammys afterparty.

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

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

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

The blue dye of Kylie’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 hair style 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.

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

Kylie 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 joined her sisters Kim and Kendall in a white mini dress during the 2010 Teen Choice Awards.

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

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

A pre-teen Kylie 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.