Kylie Jenner's beauty evolution, from kid sister on Keeping Up With the Kardashians to makeup mogul
We’ve watched Kylie Jenner grow from fresh-faced tween on Keeping Up with the Kardashians to mastermind behind one of the most successful makeup brands on the market. She may have started out as the youngest sister of the Kardashian-Jenner crew, but she became a pop culture icon in her own right. And it’s not just her fame that’s evolved over the years—her beauty and style have, too.
Kylie is known for her lips—she explained the reason she got lip injections at a young age, and recently embraced her natural lips on Instagram. The 20-year-old has tried out many different hairstyles and colors; from pink wigs to mermaid green hair to a platinum blonde bob, she’s done it all, and it’s been a delight to see her experiment.
Let’s take a walk down memory lane and check out Kylie Jenner’s beauty evolution through the years.
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When we first caught up with Kylie in the early years of KUWTK, she was a fresh-faced beauty. We can’t get over her freckles, either.
22008
Kylie was still a pre-teen in 2008, but you can see that she was starting to develop her own sense of style.
32009
For this event, Kylie added a touch of eyeliner, blush, and lip gloss. This is where she started to play with makeup a bit more.
42010
At the Burlesque premiere, Kylie wore a lot more makeup than she did in previous years. She had a smoky eye, filled in her brows, and added more blush and bronzer to finish off her look.
52011
The age of contouring was going strong, thanks to Kylie’s sister Kim Kardashian. You can see that Kylie’s makeup was very on-trend.
62012
All eyes were on Kylie’s bold red lip, poppin’ highlight, and long lashes.
72013
Kylie attended the premiere of Justin Bieber’s documentary with a glam yet casual look. She definitely has those fluttery Kardashian-style lashes.
82014
Who can forget Kylie’s dip-dyed teal hair look at the Billboard Music Awards? Aside from her eye-catching hair, she had a relatively understated makeup look.
92015
Kylie opted for a bold, matte lip and that Kardashian contour. This would eventually become her signature look.
102015
We have a feeling that when Kylie attended the Diamond Ball in 2015, she was secretly sporting a Kylie Cosmetics lip kit. Posie K, anyone?
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Once Kylie Cosmetics made its debut, the reality star started playing up her lips a lot more. She kept them matte yet soft and plush.
122016
It’s not often that Kylie goes goth, but when she does, it’s a delight. She showed off her Dead of Knight liquid lipstick and made everyone jump on the black lip bandwagon.
132016
Kylie stole the show at New York Fashion Week with her long platinum blonde hair.
142016
Once Kylie Cosmetics took off, the reality star began focusing on her lip and skin game. She opted for eyeliner-free makeup looks and only added a touch of shadow and fluttery lashes.
152016
This nude-mauve lip has become part of Kylie’s signature look.
162016
We love her soft pink lips, simple eye makeup, and fresh-faced skin.
172016
We got a rare look at Kylie without a full beat, and we were reminded of her darling freckles.
182017
Kylie looked like an ethereal goddess at the Met Gala. With her short blonde hair shining, the star’s eye makeup is the boldest part of her look. We love that she kept the rest of her makeup simple and girly.
192017
Once Kylie Cosmetics started releasing eyeshadow palettes, the reality star began to play up her eyes. In this picture, she added a lot more shadow and threw on bold lashes.
202017
Kylie’s spin on a monochromatic look is always sexy and glamorous, even when the colors are relatively nude or peachy.
212017
Is it just us, or is Kylie giving us major Kourtney vibes here?
222017
We love Kylie in a fiery lip, and this orangey-red shade is as hot as can be.
232018
In 2018, Kylie deviated from her signature style and opted for a more natural look. Her 2018 Met Gala makeup is proof of that.
242018
Kylie let her blue hair do all the talking at Coachella.
252018
Kylie has embraced the fresh-faced look in recent months, and this soft, light-winged shadow is a perfect mix of glamour and ease.
262018
Kylie chose soft, baby pink makeup that made her skin glow.
272018
Even though Kylie has gone for more subdued makeup lately, she brought back her fiery lip color for this summer look.
282018
Kylie debuted cotton candy pink hair while showing off her new Yeezy kicks. Though Kylie has played with pink hair before, we’re digging this new subtle shade.
292018
On November 16th, Kylie debuted a grayish-blonde hair color. But instead of having extremely long extensions like she normally gets with hair changes, she opted for a shorter ‘do. She wore her style sleek with a simple bun.
302019
Jenner looked like a purple mermaid princess at the Met Gala 2019 on May 6th. She doubled down on turning heads by going full teal monochromatic later that very night.
312019
The bob is the “It” haircut of summer 2019, and Kylie debuted the sleek, blunt look on June 9th in a matchy-matchy look with BFF Stassi.
322019
In honor of her birthday, Kylie showed off her Kylie Cosmetics Birthday collection with these neon shadows. She paired the makeup game with super-slicked-back hair in a low pony.
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Kylie gave us all a glimpse of her “real hair” in this video—and we love how excited she was to show it off. “Haven’t had my real hair this long since I was 15,” Jenner posted over the video.