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April 5, 2016

Kylie Jenner’s Style Evolution, From Bras Over Tees to Armani Couture

By Leah Rodriguez

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Photo: Alo Ceballos/Getty Images

Remember when, on Keeping Up With the Kardashians, Kim was devastated that Kylie Jenner wasn’t showing her enough love on Tumblr? We would probably be questioning our cool factor, too, because the youngest Kardashian, seen on the cover of Paper magazine this month, has always had a distinct personal style.

As far back as 2005, she looked at ease in everything from a camo shirt with ruffled sleeves to bra vests over T-shirts, paving the way for her ability to oscillate between Armani couture and streetwear. The 18-year-old fashion rebel of the family, who has lines at Steve Madden and Topshop and a cult lip kit, knows how to keep both her career and wardrobe interesting. See all of Jenner’s best looks and shades of pastel hair (including the blue she fought to wear at the Kimye wedding), from the front row of Prabal Gurung to the streets of Los Angeles, in our slideshow ahead.

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1 / 75 Photos
August 9, 2018 Wearing Dundas while out in Los Angeles. Photo: Hollywood To You/Star Max/GC Images
May 7, 2018 At the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art in New York City P... May 7, 2018 At the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art in New York City Photo: Theo Wargo/Getty Images for Huffington Post
April 18, 2018 Sitting court side at the Western Conference playoffs in Houston Photo: Bob Levey/Getty Images
January 10, 2017 Where: At the Marie Claire Image Maker Awards in Los Angeles. What: Dress by Balmain. Photo: Frazer Harrison/Getty Images
July 14, 2016 Where: At SinfulColors and Kylie Jenner Announce charitybuzz.com Auction for Anti Bullying in Los Angeles. Photo: Vivien Killilea/... July 14, 2016 Where: At SinfulColors and Kylie Jenner Announce charitybuzz.com Auction for Anti Bullying in Los Angeles. Photo: Vivien Killilea/Getty Images
July 7, 2016 Where: At the PrettyLittleThings.com US Launch Party in Los Angeles. Photo: Araya Diaz/Getty Images
March 24, 2016 Where: Kendall + Kylie Collection at Nordstrom Private Luncheon in Los Angeles, California Photo: Donato Sardella/2016 Donato Sa... March 24, 2016 Where: Kendall + Kylie Collection at Nordstrom Private Luncheon in Los Angeles, California Photo: Donato Sardella/2016 Donato Sardella
March 11, 2016 Where: Grand Opening of Sugar Factory American Brasserie in Orlando, Florida Photo: Gerardo Mora/2016 Getty Images
February 17, 2016 Where: New York City Photo: Josiah Kamau/2016 BuzzFoto
February 17, 2016 Where: Boss Womenswear Fall 2016 Fashion Show in New York City Photo: Antonio de Moraes Barros Filho/2016 Antonio de Moraes B... February 17, 2016 Where: Boss Womenswear Fall 2016 Fashion Show in New York City Photo: Antonio de Moraes Barros Filho/2016 Antonio de Moraes Barros Filho
February 16, 2016 Where: Vera Wang Collection Fall 2016 Fashion Show in New York City Photo: Nicholas Hunt/2016 Getty Images
February 13, 2016 Where: Alexander Wang Fall 2016 Fashion Show in New York City Photo: Jamie McCarthy/2016 Getty Images
February 12, 2016 Where: New York City Photo: James Devaney/2016 James Devaney
February 11, 2016 Where: With Bella Hadid at Kanye West Yeezy Season Three Backstage, in New York City Photo: Kevin Mazur/2016 Kevin Mazur
February 4, 2016 Where: Los Angeles Photo: JMA/Star Max/2016 Star Max
January 10, 2016 Where: InStyle and Warner Bros. 73rd Annual Golden Globe Awards Post-Party in Beverly Hills, California Photo: Jon Kopaloff/20... January 10, 2016 Where: InStyle and Warner Bros. 73rd Annual Golden Globe Awards Post-Party in Beverly Hills, California Photo: Jon Kopaloff/2016 Jon Kopaloff
December 15, 2015 Where: NIP + FAB Event in West Hollywood, California Photo: Steve Granitz/2015 Steve Granitz
December 10, 2015 Where: Second Annual Diamond Ball Hosted by Rihanna and the Clara Lionel Foundation in Santa Monica, California Photo: A... December 10, 2015 Where: Second Annual Diamond Ball Hosted by Rihanna and the Clara Lionel Foundation in Santa Monica, California Photo: Axelle/Bauer-Griffin/2015 Axelle/Bauer-Griffin
December 7, 2015 Where: LAX Photo: gotpap/Bauer-Griffin/2015 Bauer-Griffin
November 22, 2015 Where: American Music Awards in Los Angeles Photo: Frazer Harrison/AMA2015/2015 Frazer Harrison/AMA2015
October 26, 2015 Where: Los Angeles Photo: Bauer-Griffin/2015 Bauer-Griffin
October 23, 2015 Where: Olivier Rousteing & Beats Celebrate in Los Angeles, California Photo: Stefanie Keenan/2015 Stefanie Keenan
October 20, 2015 Where: Balmain x H&M Collection Launch in New York City Photo: Larry Busacca/2015 Getty Images
October 20, 2015 Where: New York City Photo: BM1/Getty Images/2015 BM1/Getty Images
October 20, 2015 Where: New York City Photo: Alo Ceballos/2015 Alo Ceballos
September 16, 2015 Where: Sugar Factory American Brasserie Grand Opening in New York City Photo: Jamie McCarthy/2015 Getty Images
September 15, 2015  Where: Vera Wang Collection Spring 2016 Show in New York City Photo: Vivien Killilea/2016 Getty Images
September 13, 2015 Where: Prabal Gurung Spring 2016 Show in New York City Photo: Andrew Toth/2015 Andrew Toth
August 30, 2015 Where: Video Music Awards in Los Angeles, California Photo: Gregg DeGuire/2015 Gregg DeGuire
July 18, 2015 Where: WSJ. Magazine and Forevermark Special Screening of Paper Towns in Los Angeles, California Photo: Michael Kovac/2015 Michae... July 18, 2015 Where: WSJ. Magazine and Forevermark Special Screening of Paper Towns in Los Angeles, California Photo: Michael Kovac/2015 Michael Kovac
July 15, 2015 Where: The ESPYS in Los Angeles, California Photo: Jon Kopaloff/2015 Jon Kopaloff
July 10, 2015 Where: Los Angeles, California Photo: Bauer-Griffin/2015 Bauer-Griffin
July 7, 2015 Where: The Gallows Premiere in Los Angeles, California Photo: Jason LaVeris/2015 Jason LaVeris
June 24, 2015 Where: Dailymail.com Seriously Popular Yacht Party in Cannes, France Photo: Marc Piasecki/2015 Marc Piasecki
June 20, 2015 Where: Los Angeles, California Photo: JMA/Star Max/2015 Star Max
June 19, 2015 Where: Grand Opening of Sugar Factory in Miami Beach, Florida Photo: Gustavo Caballero/2015 Gustavo Caballero
May 17, 2015 Where: Billboard Music Awards in Las Vegas, Nevada Photo: Jon Kopaloff/2015 Jon Kopaloff
May 14, 2015 Where: NBCUniversal Cable Entertainment Group Upfront in New York City Photo: NBCUniversal Cable Entertainment Group/2015 NBCUnive... May 14, 2015 Where: NBCUniversal Cable Entertainment Group Upfront in New York City Photo: NBCUniversal Cable Entertainment Group/2015 NBCUniversal Media, LLC
March 31, 2015 Where: Los Angeles, California Photo: MPI99/Bauer-Griffin/2015 Bauer-Griffin
March 25, 2015 Where: Los Angeles, California Photo: GONZALO/Bauer-Griffin/2015 Bauer-Griffin
March 14, 2015 Where: NIP + FAB and InStyle Tea Party  Photo: David M. Benett/2015 David M. Benett
March 14, 2015 Where: NIP + FAB Photocall in London, England  Photo: David M. Benett/2015 David M. Benett
February 16, 2015 Where: 3.1 Phillip Lim Fashion Show in New York City Photo: Craig Barritt/2015 Getty Images
February 8, 2015 Where: GQ and Giorgio Armani Grammys After-Party in Hollywood, California  Photo: Joe Scarnici/2015 Getty Images
November 23, 2014 Where: American Music Awards in Los Angeles, California Photo: Axelle/Bauer-Griffin/2014 Axelle/Bauer-Griffin
August 28, 2014 Where: DuJour Magazine's Jason Binn Celebrates Kendall and Kylie Jenner's Bruce Weber Shoot Presented by Juice Press at Lavo Rest... August 28, 2014 Where: DuJour Magazine's Jason Binn Celebrates Kendall and Kylie Jenner's Bruce Weber Shoot Presented by Juice Press at Lavo Restaurant in New York City Photo: Astrid Stawiarz/2014 Getty Images
August 24, 2014 Where: Video Music Awards in Inglewood, California Photo: Kevin Mazur/2014 Kevin Mazur
August 10, 2014 Where: Teen Choice Awards in Los Angeles, California Photo: Jon Kopaloff/2014 Jon Kopaloff
August 6, 2014 Where: The Imagine Ball in West Hollywood, California Photo: Michael Tran/2014 Michael Tran
June 27, 2014 Where: New York City Photo: Josiah Kamau/2014 BuzzFoto
June 15, 2014 Where: MuchMusic Video Awards in Toronto, Canada  Photo: George Pimentel/2014 George Pimentel
May 18, 2014 Where: Billboard Music Awards in Las Vegas, Nevada Photo: Axelle/Bauer-Griffin/2014 Axelle/Bauer-Griffin
April 12, 2014 Where: Fruttare Hangout at Coachella in Indio, California Photo: Todd Oren/2014 Getty Images
February 20, 2014 Where: Exclusive Press Preview of Tyga's Last Kings Flagship Store in Los Angeles, California Photo: Imeh Akpanudosen/2014 Im... February 20, 2014 Where: Exclusive Press Preview of Tyga's Last Kings Flagship Store in Los Angeles, California Photo: Imeh Akpanudosen/2014 Imeh Akpanudosen
November 24, 2013 Where: American Music Awards in Los Angeles, California  Photo: Jon Kopaloff/2013 Jon Kopaloff
November 18, 2013 Where: Catching Fire Premiere in Los Angeles, California Photo: Steve Granitz/2013 Steve Granitz
November 13, 2013 Where: Sugar Factory Grand Opening in Hollywood, California  Photo: Jason LaVeris/2013 Jason LaVeris
November 9, 2013 Where: Kendall and Kylie Jenner's New Holiday Collection Launch at the PacSun Store in Glendale, California Photo: Jason LaVer... November 9, 2013 Where: Kendall and Kylie Jenner's New Holiday Collection Launch at the PacSun Store in Glendale, California Photo: Jason LaVeris/2013 Jason LaVeris
October 28, 2013 Where: Ender's Game Premiere in Hollywood, California  Photo: Steve Granitz/2013 Steve Granitz
March 23, 2013 Where: Nickelodeon's 26th Annual Kids' Choice Awards in Los Angeles, California Photo: Jon Kopaloff/2013 Jon Kopaloff
December 3, 2012 Where: FM's Jingle Ball in Los Angeles, California Photo: Tommaso Boddi/2012 Tommaso Boddi
June 3, 2012 Where: 6th Annual Kidstock Music and Arts Festival Sponsored by Hudson Jeans in Beverly Hills, California Photo: Donato Sardella/20... June 3, 2012 Where: 6th Annual Kidstock Music and Arts Festival Sponsored by Hudson Jeans in Beverly Hills, California Photo: Donato Sardella/2012 Donato Sardella
December 15, 2011 Where: Grand Opening of Kardashian Khaos at the Mirage Hotel & Casino in Las Vegas, Nevada Photo: Ethan Miller/2011 Getty... December 15, 2011 Where: Grand Opening of Kardashian Khaos at the Mirage Hotel & Casino in Las Vegas, Nevada Photo: Ethan Miller/2011 Getty Images
November 17, 2011 Where: Forever 21 for Hello Kitty Collection Launch Party in Los Angeles, California  Photo: Stefanie Keenan/2011 Stefan... November 17, 2011 Where: Forever 21 for Hello Kitty Collection Launch Party in Los Angeles, California  Photo: Stefanie Keenan/2011 Stefanie Keenan
September 10, 2011 Where: Duane McLaughlin's Ready to Live Album Release Party in New York City Photo: Jerritt Clark/2011 Jerritt Clark
August 7, 2011 Where: Teen Choice Awards, Universal City, California Photo: Jeffrey Mayer/2011 Jeffrey Mayer
April 4, 2011 Where: Khloe Kardashian Odom and Lamar Odom Fragrance Launch for "Unbreakable" Photo: Jason LaVeris/2011 Jason LaVeris
March 4, 2011 Where: With Kim Kardashian at the Grand Opening of Sugar Factory American Brasserie at Paris Las Vegas  Photo: Isaac Brekken... March 4, 2011 Where: With Kim Kardashian at the Grand Opening of Sugar Factory American Brasserie at Paris Las Vegas  Photo: Isaac Brekken/2011 Isaac Brekken
February 24, 2011 Where: With Kendall Jenner at Beastly Premiere in Los Angeles, California Photo: Jean Baptiste Lacroix/2011 Jean Baptiste Lac... February 24, 2011 Where: With Kendall Jenner at Beastly Premiere in Los Angeles, California Photo: Jean Baptiste Lacroix/2011 Jean Baptiste Lacroix
May 22, 2010 Where: Sk8 for Life Benefit at Fantasy Factory in Los Angeles, California Photo: Jason LaVeris/2010 Jason LaVeris
May 10, 2008 Where: With Kendall Jenner at FM's Wango Tango Photo: Noel Vasquez/2008 Getty Images
October 14, 2007 Where: With Kendall Jenner at Keeping Up With the Kardashians Viewing Party Photo: Jeff Vespa/2007 Jeff Vespa
March 24, 2007 Where: Dash 2007 Fall Fashion Show in New York City Photo: Jeff Vespa
July 24, 2005 Where: With Bruce Jenner at Dream Foundation's "A Day to Dream"  Photo: Eric Isaacs
December 10, 2000 Where: With Bruce, Kris, and Kendall Jenner at the World Premiere of Emperor's New Groove at the El Capitan Theater in Hollywoo... December 10, 2000 Where: With Bruce, Kris, and Kendall Jenner at the World Premiere of Emperor's New Groove at the El Capitan Theater in Hollywood, California Photo: Ron Galella, Ltd./2000 Ron Galella, Ltd.
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