As a supermodel, it’s quite literally Kendall Jenner’s job to change up her look at the whim of a designer or photographer in order to fit a particular vision. From bleached brows to blonde bobs, she’s had some some pretty dramatic beauty moments in her 17 years in the spotlight — but her low-key, off-duty moments are often just as coveted. And that’s exactly what makes her best hairstyles ever such a varied bunch.
Jenner was only 11 years old when Keeping Up with the Kardashians first started filming, so of course she’s had quite the evolution in the years since. Still, even her earliest red carpet appearances made for hair moments that still hold up today. It didn’t take long for her to hone the effortlessly glamorous aesthetic that’s now considered her signature: Think piece-y, ‘90s-inspired updos, ballerina buns with wispy bangs, and beachy bobs. But of course, what would a look back at her best hairstyles be without some of more extreme experimentations, too? We pulled out some fan favorites that span from 2011 to present day that show her willingness to switch things up and her ability to make it all look flawless.
Side Braid, 2011
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Jenner was only 15 and just very early on in her modeling career when she attended the The Twilight Saga: Breaking Dawn Part 1 premiere, but her fishtail side braid was an early glimpse at what would become her trademark effortless style.
Wet Look, 2014
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For her appearance at the 2014 Teen Choice Awards, the model was an early supporter of the wet look hairstyle celebrities still love a decade later.
Bun with Bangs, 2015
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Jenner opted for long, wispy bangs and a top knot for her appearance at the American Music Awards in 2015. The fringe was a dramatic change-up for the reality star, and created one of her most memorable updos to date.
Bubble Ponytail, 2016
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While Jenner often gravitates to more undone, less-is-more hairstyles, her dramatic bubble ponytail made an edgy statement that felt so apropos for the MTV Movie Awards.
Old Hollywood Waves, 2017
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Just a year later, Jenner chopped her long hair into a jaw-length bob that she styled so many chic ways — including these vintage-inspired waves from Harper’s BAZAAR’s ICONS Party.
Beachy Bob, 2018
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The model wore her slightly grown-out bob in tousled beach waves while attending Alberta Ferretti’s runway show at Milan Fashion Week. Paired with barely-there makeup, the look totally exemplified her laid-back beauty style.
Ombré Tips, 2020
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Some of Jenner’s hair color changes are major, and some are a little more low-key. In terms of the latter, her caramel balayage in 2020 added just the right amount of dimension to her tousled long bob.
Strawberry Blonde, 2022
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Just a few years later, the supermodel took the plunge with a more dramatic change in color. Though her strawberry blonde hue didn’t last long, her redheaded era was so soft and glamorous.
‘90s Updo, 2023
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When it comes to a perfectly imperfect updo, few do it better than Jenner. And her piece-y, loosely pinned-up style from the Vanity Fair after party in 2023 actually went viral with fans trying to recreate the exact look.
Soft Blonde Waves, 2024
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Jenner’s freshly blonde bob was just begging to have its Marilyn moment, which got for the Academy Museum of Motion Picures Gala. The 818 founder’s soft waves totally channeled Monroe’s iconic Gentlemen Prefer Blondes hair.
