STYLE EVOLUTION

Kylie Jenner Has Undergone a Complete Style Transformation

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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 mother. She was born into a reality-television dynasty, and as a result, she grew up in the spotlight, accompanying her parents on the red carpet and frequently twinning with Kendall Jenner, the sister just two years her elder. But over time, Kylie’s cultivated a look that sets her apart from her closest sibling and aligns her more directly with her Kardashian half-sisters, filling her closet with shimmering Balmain looks and plenty of streetwear. (She’s also a brand ambassador for Puma and a noted fan of Adidas track wear.) And despite her fame, she managed to stay out of the spotlight while pregnant with her daughter, Stormi Webster. See Kylie Jenner’s transformation from tween star to Olivier Rousteing muse and self-described “cool mom,” here.

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Kylie Jenner, Caitlyn Jenner (formerly Bruce Jenner), Kendall Jenner, and Kris Jenner at the world premiere of The Emperor’s New Groove in Hollywood, California, December 2000.

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Kylie Jenner at the Matrix at A Time for Heroes Celebrity Carnival Benefiting the Elizabeth Glaser Pediatric AIDS Foundation in Los Angeles, June 2008.

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Kendall, Kris, and Kylie Jenner at the 102.7 KIIS-FM’s Wango Tango in Irvine, California, May 2009.

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Kylie Jenner at the release party for Selena Gomez’s Kiss and Tell in Hollywood, September 2009.

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Kendall Jenner, Kim Kardashian, and Kylie Jenner at the Teen Choice Awards in Universal City, California, August 2010.

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Kendall and Kylie Jenner at the premiere of Justin Bieber: Never Say Never in Los Angeles, February 2011.

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Kendall and Kylie prove their twinning days aren’t behind them at the premiere of Prom in Hollywood, April 2011.

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Kylie Jenner at the Race to Erase MS in Century City, California, May 2012.

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Kylie Jenner at Fashion’s Night Out in Los Angeles, California, September 2012.

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Kendall and Kylie Jenner, honing their fashion consultant chops, go on Good Morning America to discuss spring trends, February 2013.

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Kylie Jenner wore a dress by Msfts, the label by then-reported boyfriend Jaden Smith, to the Kids’ Choice Awards in Los Angeles, March 2013.

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Kylie Jenner opted for white and nude, a palette she’d come to favor down the line much like sister Kim Kardashian, at the MTV Movie Awards in Culver City, California, April 2013.

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Kylie Jenner opted for a sleek black two-piece look to attend the premiere of After Earth (the movie fronted by rumored boyfriend Jaden Smith) in New York, May 2013.

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Jenner opted for a tonally appropriate graphic tee to walk the red carpet with Jaden Smith at the premiere of Ender’s Game in Hollywood, October 2013.

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Kylie Jenner, in Maiyet and Giambattista Valli, debuted a new hair style when she walked the red carpet with sister Kendall at the American Music Awards in Los Angeles, California, November 2013.

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Kylie Jenner in Alex Perry with Louboutin heels at the Billboard Music Awards in Las Vegas, Nevada, May 2014.

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Jenner opted for an orange Nicolas Jebran minidress, contrasting with her sister’s Fausto Puglisi, at the MuchMusic Video Awards in Toronto, Canada, June 2014.

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Kylie Jenner in Alexandre Vauthier with Gucci heels at the MTV Video Music Awards in Inglewood, California, August 2014.

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Jenner opted once again for Alexandre Vauthier, this time in burgundy, for the American Music Awards in Los Angeles, California, November 2014.

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Kylie Jenner in Steven Khalil at the GQ Grammys afterparty in Hollywood, California, February 2015.

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Kylie Jenner appeared front row at the 3.1 Phillip Lim show — wearing Phillip Lim, naturally — during New York Fashion Week Fall 2015 in New York, New York, February 2015.

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Completing the arc that brought her into Olivier Rousteing’s fold, Kylie Jenner wears Balmain at the Billboard Music Awards in Las Vegas, Nevada, May 2015.

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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 Jenner wears a Cushnie et Ochs top with Alaïa leggins and a Kimora Lee Simmons coat for the premiere of The Gallows in Los Angeles, California, July 2015.

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Kylie Jenner in Shady Zeineldine at the ESPYs in Los Angeles, California, July 2015.

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Jenner steps out with a bleached ‘do and a new pantsuited look, sitting front row at the Prabal Gurung show during New York Fashion Week Spring 2016 in New York, New York, September 2015.

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Wearing Balmain x H&M, Jenner appeared at the launch of the capsule collection in New York, New York, October 2015.

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A regular at the American Music Awards, Jenner went custom for the 2015 edition in Bryan Hearns in Los Angeles, California, November 2015.

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Also a regular at Vera Wang, though perhaps an unexpected one, Jenner went full-on Kylie Minogue during the Fall 2016 season at New York Fashion Week in New York, New York, February 2016.

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Jenner called on Olivier Rousteing to outfit her for last year’s Met Gala, wearing custom Balmain to the Costume Institute gala for Manus x Machina in New York, New York, May 2016.

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Jenner sat front-row at Jonathan Simkhai in a denim ensemble with a skull cap during New York Fashion Week Spring 2017 in New York, New York, September 2016.

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When you’re a Kardashian, even the runway won’t do — Jenner went custom once again for the Golden Globes in a silver Labour Joisie gown in Beverly Hills, California, January 2017.

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On the opposite coast, Jenner attended Alexander Wang’s guerrilla uptown show during New York Fashion Week Fall 2017 in New York, New York, February 2017.

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Just prior to Coachella this weekend, Jenner continued to make the biggest statements, foregoing the usual fringe-and-floral festival look in favor of purple Balenciaga boots at the PrettyLittleThing launch in Los Angeles, California, April 2017.

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She continued to attend PrettyLittleThing events at Coachella, too, here, with fresh green hair and in one of the brand’s sparkly minidresses in Indio, California, April 2017.

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Kylie Jenner out in Soho, New York, April 2017.

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Kylie Jenner, in home team colors, at a Houston Rockets game with rumored boyfriend Travis Scott in Houston, Texas (the rapper’s hometown), April 2017.

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Kylie Jenner heads out to Travis Scott’s birthday party in all-black in New York, New York, April 2017.

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Kylie Jenner in a custom Versace dress at the Metropolitan Museum of Art Costume Institute gala for ‘Rei Kawakubo: Art of the In-Between’ in New York, New York, May 2017.

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Tyga and Kylie Jenner attend the Front Row for the Philipp Plein Fall/Winter 2017/2018 Women’s And Men’s Fashion Show at The New York Public Library on February 13, 2017 in New York City. Photo courtesy of Getty Images.

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Kylie Jenner pranked family members with her look-alike Madam Tussaud’s wax figure, which wears the custom Balmain dress she wore to the 2016 Met Gala, in Los Angeles, California, July 2017.

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Kylie Jenner and Kim Kardashian attend the Louis Vuitton Menswear Spring/Summer 2019 show as part of Paris Fashion Week Week on June 21, 2018 in Paris, France. Photo courtesy of Getty Images.

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Kylie Jenner and Travis Scott attends Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at Metropolitan Museum of Art on May 7, 2018 in New York City. Photo courtesy of Getty Images.

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Kylie Jenner is seen in Chinatown on May 8, 2018 in New York City. Photo courtesy of Getty Images.

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Kylie Jenner and Travis Scott leave after Game Two of the first round of the Western Conference playoffs at Toyota Center on April 18, 2018 in Houston, Texas. Photo courtesy of Getty Images.

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Kylie Jenner seen out and about in Manhattan on May 5, 2018 in New York City. Photo courtesy of Getty Images.

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Photo by Paul Zimmerman/WireImage

Kylie Jenner attended the 2018 MTV Video Music Awards in a white suite dress with silver heels.

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Photo by David Crotty/Patrick McMullan via Getty Images

Wearing a sculptural pink Balmain couture outfit, Kylie Jenner attended the 61st Annual Grammy Awards at Staples Center on February 10, 2019 in Los Angeles, California.

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Photo by Dia Dipasupil/FilmMagic

Wearing purple Versace Atelier, Kylie Jenner attended The 2019 Met Gala Celebrating Camp: Notes on Fashion at Metropolitan Museum of Art on May 06, 2019 in New York City.

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Photo by Toni Anne Barson/WireImage

Kylie Jenner opted for a glittery gunmetal gown at the 2020 Vanity Fair Oscar Party at Wallis Annenberg Center for the Performing Arts on February 09, 2020 in Beverly Hills, California.

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Photo by IAMKEVINWONG/MEGA/GC Images

Kylie Jenner is seen arriving at The Nice Guy on March 25, 2021 in West Hollywood, California in a monotone red getup.

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Photo by Gotham/GC Images

Wearing green Jean Paul Gaultier, Kylie Jenner departs the 2021 Parsons Award event on June 15, 2021 in New York City.