Kylie Jenner’s look has changed considerably since she first rose to fame on her family’s hit reality show Keeping Up with the Kardashians. When she was younger, she opted for quite a natural look and would wear light, barely-there makeup. As she grew into her teenage years, her appearance really started to change, especially because she began to experiment with makeup. It’s been interesting to see Kylie grow and evolve over the years, so follow along as we retrace Kylie’s face evolution from her early reality TV days to now:
Premiere of Easy A – September 2010
Kylie Jenner attended the premiere of Easy A when she was around 13 years old in 2010. Her makeup was quite natural in comparison to her later years and she wore a little eyeliner, mascara, a coral blush and light gloss on her lips. While her look was by no means over the top, it is quite bold for someone so young and she looks much older than 13 years old!
Fragrance Launch — April 2011
In the spring of 2011, Kylie Jenner stepped out for a fragrance launch at The Redbury hotel in Los Angeles. Her hair appeared a little unkempt, but it was clear she began experimenting a little more with heavier makeup and vibrant lipstick shades. Her features appear more chisled and it’s clear she’s in the midst of maturing into her teenage years.
Teen Choice Awards — August 2011
In 2011, Kylie continued to make appearances at high-profile celebrity events like the Teen Choice awards. This summer evening she stepped out with light face makeup and a heavier bronzed smokey eye. While we love the golden shadow, her bottom eyeliner seemed a bit heavy, but this was simply the trend at the time. She rocked a natural lip without exaggerating with liner, which was something that would change considerably in the future. Overall, her look was youthful, fun and appropriate for her age.
Hollywood Style Awards – November 2011
In November 2011, Kylie continued to attend events and pose for the red carpet looking dolled up to the nines. This evening, Kylie and her older sister Kendall took home the Stylish Sisters awards. It was clear by this point she was getting more into makeup and experimenting with what shades and styles worked for her. While we love how the black eyeliner contrasts with her chocolate eyes, we’re not sure this shade of foundation worked for her! It seemed to wash out her complexion and be a tone or two too light.
Premiere of The Hunger Games – March 2012
In 2012, Kylie attended the premiere of The Hunger Games with her sister Kendall. She dressed to the nines for the event, wearing a short white mini dress, some sky-high nude pumps and a little more dramatic makeup. Kylie was well on her way to becoming an adult at this point and becoming fully launched into the spotlight. She and her sister Kendall had stopped attending high school to focus on their careers and had enrolled in a homeschooling program. Her look, for this event, was significantly more dramatic. It’s clear she learned how to properly match her foundation to her skin and used some bronzer to get a glowy, sun-kissed look.
Kid’s Choice Awards — March 2013
Kylie Jenner stepped out in early 2013 wearing quite sophisticated, polished makeup. Her skin was matte and flawless, while her lips were perfectly lined with a pop of red. Her eye makeup was quite natural, simply opting for a little eyeliner and mascara. We quite enjoy this version of Kylie! Her makeup is still dramatic enough for a red carpet but doesn’t appear cakey or over the top by any means.
Premiere of Ender’s Game – October 2013
The 16-year-old reality TV star started to look a little different when she showed up at the premiere of Ender’s Game in 2013. Kylie Jenner was pretty busy professionally at this point. She was doing three to four hours of homeschool a day and then would spend the rest of the day working. She was dabbling in beauty products, music and science fiction. In terms of her look for the event, Kylie’s lips looked a bit fuller, but this could be because of the fact that she’s clearly learned how to strategically apply makeup now. She’s contoured her cheeks, exaggerated her eyebrows and brightened her under eyes, which are all makeup techniques typically used by professionals. We think she looks stunning!
Justin Bieber Believe Premiere — December 2013
A few months later in December 2013, Kylie stepped out to attend Justin Bieber’s Believe premiere with a fresh hairstyle. Changing up her look is something that Kylie would do often in years to come, so this change marked just the beginning! She chopped a few inches off her hair and played with fun dip-dyed chestnut tips, which was a huge trend at the time. For her makeup, she’s clearly mastered the flawless skin look with her foundation and opted for a softer grey eye and mauve lip.
Billboard Music Awards — May 2014
By the time early May rolled around in 2014, it was clear that Kylie had matured significantly! At 17-years old, she stepped out at the Billboard Music Awards with an edgy new look that consisted of a blue-tinted bob and chunky silver choker. She was trailblazing a path for trends with everything from her makeup to her hair to her style. We can’t help but notice, however, how significant of a change her look made in a few short months. Her lips were fuller, her hair more tamed and her makeup was the perfect balance of glam but still natural.
Lavo Restaurant Event — August 2014
In August 2014, the reality star was on her way to full-blown stardom with the glam red carpet makeup to match. Rather than the heavy liner of her pre-teen and teenage years, in 2014 Kylie tends to focus her eye makeup on long, wispy lashes instead. Her skin is flawless and she topped her demure look with a brick red lip, that at this point, were clearly quite enhanced by the beginning phases of her lip filler years.
American Music Awards – November 2014
In late 2014, Kylie Jenner debuted an even more mature and obviously enhanced look for the American Music Awards. Her lips are super plump, which lead many of us to assume that she had lip injections but it took her a while to admit to them. “You guys have watched me grow up since I was 9. My face is going to get different. Now, I know how to do my makeup, contour, and everything. I’m not against surgery. I’d never say no, but I don’t desire it right now,” she said at the time. Aside from her lip enhancement, her face has naturally matured and become more sculpted and adult-like. She’s also become even more skilled with her makeup application by rocking a natural glam smokey eye, perfectly arched brows and a deep plum lip that played strategically off the colors of her dress.
Paper Towns Premiere — July 2015
In July 2015, Kylie stepped out without an entirely new hair color, which is something we had began to expect from her! This time, the star opted for a faded ice blue color lob that worked well with her sunkissed summer skin. She contrasted the blue tones of the hair with a pink-tinted smokey eye and a soft wash of rose on her lips.
The Diamond Ball — December 2015
A few months later in December 2015, Kylie stepped out back to a natural color with her hair, which had many speculating that all her drastic hair changes were actually wigs. This time, her hair was jet black, long and styled in wispy waves. For her makeup look, she opted for a full glam look with a bronze smokey eye and her classic mauve lip color.
Pretty Little Thing Launch — July 2016
In mid-summer 2016, Kylie Jenner stepped out for the Pretty Little Thing Launch with even more defined makeup. She wore dramatic false lashes and clearly grew out her eyebrows to a thicker, more arched shape. She wore a pop of pink blush on her cheeks and her lips were looking more full than ever, especially because on top of the enhancements, she also overlined her lips for more definition.
Met Gala — May 2017
A year later, in 2017, Kylie Jenner shocked us all by stepping out with a head of platinum blonde hair! The Kardashians are known for shocking with their makeup and hair, so this wasn’t entirely out of the ordinary for Jenner. While brunette will always be our favorite on Kylie, this pop of icy blonde was a nice change for an experimental event like the Met Gala. As for her face, Kylie rocked a natural nude look by skipping the eyeliner and opting for soft champagne colors on her lids with long lashes. Her lips were still quite full, but more understated with a nude tint on them.
Paris Fashion Week — June 2018
In June 2018, Kylie Jenner attended Paris Fashion Week debuting her natural jet black hair styled in a slick updo. Her makeup appeared quite natural with no heavy shadows, which allowed her long lashes and perfectly arched brows to steal the show. Her skin is dewy and bright and she topped the look with a ’90s-inspired brown tone lip. The 2018 appearance was one of the few of the year because she spent many months in hiding trying to hide her pregnancy from the media.
MTV Video Music Awards — August 2018
In the summer of 2018, Kylie shocked the world again when she made the drastic decision to dissolve all her lip injections shortly after giving birth to her daughter, Stormi, in February. Sources shared that Kylie’s new baby was a huge reason behind deciding to dissolve her fillers as well. “During Kylie’s pregnancy, she wasn’t getting her usual fillers or putting on much makeup,” a source explained. “Kylie really fell in love with the natural look, and wanted more of that, so she decided to stop putting filler in her lips.”
Grammy Awards — February 2019
In 2019, Kylie was pictured at the Grammy Awards in February, a year after giving birth to her daughter, Stormi. For the appearance, she rocked a pink-tinted eye, nude lip, and a tousled updo. The look felt very quintessential Kylie with the neutral shades and bold overlined lip, which has grown to become a signature style for her.
Paris Fashion Week — September 2022
In September 2022, Kylie attended shows at the fall Paris Fashion Week. In this photo, she was pictured attending the Acne Studios Womenswear Spring/Summer 2023 show. She kept her look sleek and natural with a light eye look with neutral shadows and a minimal swipe of mascara. She wore a flush of warm blush on her cheeks and rocked her signature bold lip look with a deep lip liner. For her hair, she kept things sleek with two small strands hanging around her face for a high-fashion twist.