Kylie Jenner's Style Transformation: From Cute to Va-Va-Voom

Stefanie Parker | Nov 26, 2019 Celebrities
Kylie Jenner's Style Transformation: From Cute to Va-Va-Voom
Image: Kristian Dowling/KK/Getty Images for GI

Kylie Jenner
Kristian Dowling/KK/Getty Images for GI

Sure, she's rich, successful, and beautiful, but when it comes to being fashionable, Kylie Jenner is in a league of her own -- and there are only three words to describe her recent style -- va va voom. The makeup mogul has been turning heads just about everywhere she goes for quite some time now, and for good reason ... she can make a paper bag look hot. But it hasn't always been that way. Long before the 22-year-old self-made billionaire became a fashion staple at every single red carpet event in Hollywood, she was just the awkward little sister of Kim, Kourtney, and Khloé Kardashian, often being overshadowed. 

But boy, have the tables certainly turned for sweet little Kylie. 

Today, not only is she the richest of the Kardashian klan (she just sold a majority stake of her Kylie Cosmetics company to Coty for a whopping $600 million!), but she's arguably the most popular Kardashian sister, seemingly rivaling Kim for that coveted spot. By the time Kylie turned 18, Kim was well aware that her baby sister was nipping at her heels -- but it was something she embraced. 

"I love it, like, I love it. I need some time off," she said of Kylie "dethroning" her while shooting a video for her sister's app. (Kim quickly added that Kylie would need to put in "a few more years" before she actually takes her throne.) "Who better to pass on knowledge to my baby sister, rather than a random non-family member?" she asked.

But according to Kylie, she's not interested in Kim's throne ... she's just fine making her own throne -- better yet, her own castle. "I think people forget that me and Kim are sisters," she told Entertainment Tonight in 2016. "We're not in a competition. We're completely different people."

Different people, sure ... but it's hard to deny that Kylie has transformed into a mini-Kim over the years. 

Take a look.

  • Sweet & Innocent Start

    1
    Kylie Jenner 2011
    Splash News

    Way back when! 

    Kylie donned a casual maxi dress on the way to a Vera Wang dress fitting for Kim's wedding to Kris Humphries (LOL, memories) back in 2011. Nothing about this look screams fashionable A-lister ... and she appeared to be OK with that at the time. If only she knew then that she'd become one of the biggest fashion icons.

  • Hot Pink Tips

    2
    Kylie Jenner 2011
    Splash News

    Making moves! It was at the Abbey Dawn by Avril Lavigne runway show in 2011 where Kylie started to first show signs of wanting to stand out from the crowd, and she did just that with this look. She proudly showed off her hot pink hair tips and dark eye makeup on the red carpet. 

  • Bright Red Pout

    3
    Kylie Jenner 2012
    Splash News

    Look at those red lips! Kylie happily posed at the Kardashian Khaos store (which no longer exists -- boo!) in Las Vegas back in 2012, but kept things covered up. The reality star was all business at this point in her style game.

  • Showing Some Skin

    4
    Kylie Jenner 2013
    Splash News

    Kylie appeared to be much more comfortable with her body in 2013 at the After Earth movie premiere in NYC. Not only did she show off some midriff, but her asymmetrical skirt was a daring new look for her. She also started to experiment with her hair texture, opting for sexy, Kardashian-esque curls this time around.

  • Errands in a Leather Mini Skirt

    5
    Kylie Jenner young
    Splash News

    Fashion never takes a day off ... because who doesn't go shopping in a sexy leather skirt? Kylie proved that being stylish was at the forefront of her mind while running errands with friends in Studio City, California, back in August 2013. 

    Looking good, Ky!

  • Chopping the Bangs

    6
    Kylie Jenner American Music Awards
    Splash News

    Look at those bangs! Kylie attended the 2013 American Music Awards and rocked some edgy hair fringe for the occasion. While she showed off some midriff on the red carpet, her look was overall fairly modest. Still, the change-up with the hair was a step in the right direction for Ky.

  • Edgy on the Carpet

    7
    Kylie Jenner 2013
    Splash News

    She doesn't need much to look trendy. This was Kylie's go-to look for quite some time -- a statement T-shirt paired with a skirt and stylish heels. It definitely screams, "I know I'm hot, but I'm not trying too hard," and it certainly worked for her.

  • Dark & Mysterious

    8
    Kylie Jenner 2013
    Splash News

    Long before the makeup mogul invented Lip Kits, Kylie experimented with other makeup brands. "I was insecure about my lips, and lipstick is what helped me feel confident," she previously told Evening Standard. This dark cranberry lip perfectly paired with her skin-tight grey dress at The Hunger Games: Catching Fire premiere in November 2013.

  • Feeling Turquoise

    9
    Kylie Jenner 2014
    Splash News

    By 2014, Kylie was rocking a different hair color each week, but turquoise was a favorite for a long period of time -- and she often experimented with different variations of the color. At the Billboard Music Awards, this reality star kept her dress simple, so it didn't distract from her wild hair.



  • Comfortable in Her Own Skin

    10
    Kylie Jenner 2014
    Splash News

    That's not just midriff anymore, that's her whole dang torso. By late 2014, Kylie clearly felt more comfortable showing off her body, and that includes her (suddenly larger) lips. "I really wanted bigger lips. I would over-line my lips with lip liner just to create the illusion of bigger lips," she revealed on her reality show, Life of Kylie.

  • Sheer Sight

    11
    Kylie Jenner
    Splash News

    Whoa there! In March 2015, Kylie served as the brand ambassador for cosmetics company, Nip + Fab. Her lips were now a constant accessory and she started to wear clothes that accentuated her curves -- like a completely sheer shirt paired with a black bra, for example.

  • Green With Envy

    12
    Kylie Jenner Sugar Factory
    Splash News

    Kylie somehow managed to make green hair look sexy, and fans couldn't wait to see which color she would sport next. But a secret she kept from the public for a while was that she wasn't actually dyeing her hair? She was wearing wigs. "I started wigs, and now everyone is wearing wigs," Kylie previously told Marie Claire. "I just do whatever I want to do, and people will follow."

  • Taking Fashion Risks

    13
    Kylie Jenner Balmain
    Splash News

    By 2016, Kylie was a fashion icon -- so she had no problem taking risks like this daring Balmain number she wore after the Met Gala. She paired it with a simple blunt bob, which was a big change for her. The over-the-knee boots added the extra sexiness that was missing from the overall look.

  • Blondes Have More Fun

    14
    Kylie Jenner jumpsuit
    Splash News

    Ample cleavage? Check! Curve-hugging body suit? Check! Bleached blond hair? Check! Kylie had no problem showing off every inch of her body by 2015. She somehow made this head-to-toe cream colored one-piece look effortless. 

  • Seeing Color

    15
    Kylie Jenner 2016
    Splash News

    Up until this point, Kylie kept her color scheme fairly monochromatic, but at the PrettyLittleThing's #PLTxUSA launch party in July 2016, she finally spiced things up with some color. Bright orange paired perfectly with her long dark locks and beautiful tan.

  • Having More Fun

    16
    Kylie Jenner purple
    Splash News

    Who else could pull off a look like this? Kylie Jenner donned this daring purple number at Marie Claire's Image Maker Awards in 2017 and we're assuming she turned many heads in the process. She clearly wasn't messing around with her style game. 

  • Pop of Color

    17
    Kylie Jenner purple boots
    Splash News

    Oh hey there, boots. Kylie showed off her playful side with these bright purple over-the-knee boots at PrettyLittleThing's Shape x Stassie Campaign Launch in 2017. At this point, she'd gone back to her dark haired roots and hung her colored wigs up in the closet.

  • Va-Va-Voom

    18
    Kylie Jenner 2018
    Splash News

    She's a hot mama and she knows it. The reality star had welcomed daughter, Stormi Webster, just a handful of months prior to wearing this latex number in September 2018. Kylie proudly showed off her post-baby body while attending The Nice Guy bar in West Hollywood.

  • Perfect Accessory

    19
    Kylie Jenner Stormi
    Splash News

    There she is! By 2019, Stormi became the perfect accessory for the mom of one, often carrying her on her hip and looking flawless while doing it. Kylie flashed her toned tummy in the airport just one day after the 2019 Met Gala. Both Kylie and Stormi are clearly a fashion forward duo.

  • White Hot Curves

    20
    Kylie Jenner white dress
    Splash News

    Curves for days! Kylie attended then-boyfriend Travis Scott's Look Mom I Can Fly premiere in August in this hip-hugging, white dress. This was the first red carpet event where Stormi, Travis, and Kylie posed together. Seriously, how great does this mama look?

celebrity style celebs

More Slideshows