Kylie Jenner’s Face EvolutionPublished on April 25, 2019. Updated November 27, 2019
Kylie Jenner’s look has changed considerably since she first rose to fame on her family’s hit reality TV 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:
KIIS FM’s Wango Tango — May 2009
Kylie Jenner has been in the spotlight from her preteen years all the way into her teenage years and now, motherhood. Some of her earliest red carpet appearances occurred in 2009 and it’s obvious she is quite young! She’s photographed here at the 2009 KIIS FM Wango Tango awards which appear to be the beginning stages of her experimentation with makeup. She still has many of her baby features, but the edgy bang and dark liner definitely foreshadow her style for the years to come.
Record Release Party — September 2009
Later in the year in September, Kylie was photographed at a record release party. During the months between, she grew out her bangs to a softer, side part which we actually really like on her since it feels feminine and shows off her features better! She’s still experimenting with makeup and rocked charcoal-lined eyes and a glossy lip to the event.
KIIS FM’s Wango Tango — May 2010
The following May in 2010, Kylie stepped out at the Wango Tango event one full year later. It’s clear she’s definitely matured in her face over the course of the year and has learned to style her hair and makeup in a more glamorous, red carpet-worthy way. From the bouncy curls to the perfect winged liner, this appearance was both adorable and fabulous!
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 even 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.
Seventeen Party — August 2012
In the summer of 2012, Kylie stepped out to a Seventeen party at the W Hotel in Los Angeles. By this point, she had garnered quite a bit of attention as a reality TV star. For the event, Kylie donned a full face f makeup from the smoked out eye, berry lip and full coverage foundation.
Jingle Ball — December 2012
Later that year in December, Kylie stepped out for an appearance at KIIS FM’s 2012 Jingle Ball in LA. On this close up of her face, you can see that Kylie is still experimenting with her makeup and wasn’t quite mastered the art of taming an oily T-zone! We love, however, that her natural skin is still prevalent and how well her black liner contrasts with her chocolate eyes.
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 questionable 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.
Nip + Fab Photocall in London – March 2015
When Kylie stepped out at the Nip + Fab Photocall in March 2015, the 17-year-old reality TV star had clearly changed even more. While we love Kylie’s golden eyes and red lip, her matte face makeup photographed a little cakey here, but luckily as she grows, she learns how to make her skin look significantly more natural and dewy. This month also signified the time where she finally confessed that she did have her lips done and admitted she had previously lied. She justified her decision by explaining, “I didn’t want people to think you had to get your lips done to feel good about yourself. But they thought it was crazier that I was lying about it because it was so obvious.”
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.
Nordstrom Launch Event — March 2016
In March 2016, Kylie stepped out at an event for her Nordstrom line Kendall + Kylie at Chateau Marmont. By this time, she admitted to her lip injections and it was no longer a secret. In her later years, Kylie reflected on this time and admitted that she was always insecure about her lips, which ended up being the inspiration behind her successful lip kit line. “I have really small lips, and it was like one of my first kisses and a guy was like, ‘I didn’t think you would be a good kisser because you have such small lips.’ But I took that really hard,” she explained.
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.
New York Fashion Week — September 2016
In the fall of 2016, Kylie stepped out with yet another hair change. This time, blonde! She was photographed at the Louis Vuitton show at Paris Fashion week rocking mid-length golden blonde waves which she complemented with a dark, gunmetal smokey eye and nude lips.
Pretty Little Thing Launch — April 2017
The following year in 2017, yet again, Kylie stepped out with new hair, which definitely confirmed the wig theory. Her color of choice this time around was lime green which she wore at a cropped length skimming her shoulders. Her makeup was quite neutral with heavy lashes, a tiny of coral on her cheeks and nude lips.
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
We love seeing in 2019 how Kylie has come full circle! She’s experimented with her look, grew her love of makeup with a successful lip kit brand, but at the end of the day, she’s proved she’s found a way to be confident in her own skin. She was recently 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.
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