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Only in the Kardashian-Jenner family would international supermodel Kendall Jenner be considered the *least* adventurous when it comes to fashion and beauty. Taking a look at the style metamorphoses of trend-defining sister Kim, hair transformation pioneer Khloé, makeup maven Kylie, and style chameleon Kourtney, Kendall’s beauty evolution may look pretty tame — but that doesn’t mean she hasn’t undergone her fair share of drastic makeovers.
As one of her generation’s most famous faces, the second youngest KarJenner has been a blonde, brunette, and redhead in the span of just a few years. She’s worn some truly wild makeup and even donned huge (temporary) tattoos, but at the end of the day, Kendall’s biggest beauty moments are mainly limited to her professional life. Off the runway and away from the red carpet (aka at home and on her family’s reality TV show, The Kardashians), this KarJenner is mostly a jeans and T-shirt kind of gal.
Even so, when you’ve spent years modeling for some of the biggest names in the fashion world, you’re bound to have rocked a few dozen daring beauty looks. As you’ll see in Kendall Jenner’s beauty evolution, that’s definitely the case for the world’s highest-paid supermodel. From faux piercings to bleached brows, slicked-back bangs to brightly dyed locs, Kendall’s been there and done that for almost every beauty trend imaginable.
October 2007: Li’l Kendall Jenner With No Makeup
At one of the first screenings of Keeping Up With The Kardashians in October 2007, Kendall (left) posed with little sister Kylie (right). The two were as fresh-faced as you’d expect from preteens and all of Kendall’s freckles were on full display.
May 2009: Young Kendall Jenner Wearing Eyeliner
In just two years’ time, Kendall was ready to break out the makeup, kind of. While walking a red carpet in May 2009, the almost-teen wore a bit of eyeliner that gave off some angsty tween vibes.
August 2009: Kendall Jenner With Metallic Inner Eye Makeup
Continuing on her makeup experimentation journey, Kendall attended the 2009 Teen Choice Awards wearing a bit of blush, a slight contour, and a pop of metallic white-gold eyeshadow on her tear ducts.
August 2011: Kendall Jenner’s First Smokey Eye
New look, who dis? At the 2011 Teen Choice Awards, Kendall rocked one of her first major beauty looks: a fully-lined smokey eye. Her smudgy glam was paired with a slicked-back mohawk braid, which let her bold makeup take the center stage.
November 2013: Kendall Jenner Wears A Bold Red Lip
The aughts were *the* era of liquid matte lipstick and Kendall dipped her toes into the trend for the 2013 American Music Awards. Her vibrant and cool-toned red lip was a departure from her usual natural approach to glam.
June 2015: Kendall Jenner With Piecey Bangs
Nothing says “I’m young and cool in the aughts” like a set of piecey bangs falling into your eyes, which is the exact look Kendall rocked on the 2015 American Music Awards red carpet. Complete with a sleek top knot, matte contour, and a glossy lip, this was the ultimate cool girl look at the time.
June 2016: Kendall Jenner With Slick Side Bangs
March 2016: Kendall Jenner With Bleach Blond Hair
In March ’16, Kendall went bold blond for the Balmain Fall/Winter runway show. The ultra-pale color left half an inch of her natural roots exposed and was toned to an icy near-white.
September 2016: Kendall Jenner With Locs
Just a few months later, Kendall was on the runway again with a wildly different look. In Sept. ’16, she walked the Marc Jacobs runway during New York Fashion Week with a crown of rainbow locs.
March 2017: Kendall Jenner’s Punk Rock Smokey Eye
On the Balmain Fall/Winter runway in March ’17, Kendall wore one of her most major looks to date. Not only was the lip jewelry she wore an instantly iconic — albeit impractical — accessory, but her shiny mohawk braids and reverse cat eye smoked -out makeup were a thing of punk rock beauty.
September 2017: Kendall Jenner With Green Hair
In 2017, Kendall continued her habit of debuting daring hair transformations on the runway. During Milan Fashion Week, the model walked the Fendi Spring/Summer runway with a rich, blue-toned shade of green hair on one side of her hair and her natural hair color on the other.
September 2018: Kendall Jenner With A Sleek Lob
Taking a break from wild hair transformations, Kendall was spotted in SoHo in September 2018, rocking a shoulder-skimming lob. The cut was sharp, sleek, and very much aligned with Jenner’s easy breezy, off-duty model vibes.
September 2019: Kendall Jenner With Blond Hair
For Milan Fashion Week in 2019, Kendall walked the Fendi Spring/Summer runway with long bangs and blond hair. The shade toed the line between buttery and bleachy and showed off her dark roots.
February 2022: Kendall Jenner With Red Hair
May 2022: Kendall Jenner With Bleached Eyebrows
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