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Despite her insider connections, it really does seem like the odds were stacked against Kendall Jenner when she first sought out top modeldom. After so many years baring all their business of reality TV, her famous family’s reputation could either work for or against her — luckily for Jenner and her legion of fans, it wasn’t long before she found her niche in the fashion industry. Those who have been watching her for a while, though, know that the second-to-youngest sister was always destined for greatness beyond just the larger Calabasas area. Looking back at Jenner’s beauty evolution, it’s clear that her penchant for aesthetic experimentation and incorporating edge into even the most unexpected looks was preparing her for one seriously huge career.
These days, Jenner is part of a new, modern class of supermodel, who dominate social media feeds and runways in equal measure. Part of her success is a willingness to try new things and transform to suit different designer visions — she’s bleached her brows, gone red and blonde, and even wore face tattoos for assorted fashion shows. Off-duty, Jenner mixes those same daring elements with a distinctive sporty-sophisticated style. Is it any wonder she’s been considered the highest-paid model for several years now?
Just below, look back at Jenner’s journey from reality star to supermodel status.
Sister Act, 2014
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When Jenner and her younger sister first stepped into the spotlight as young adults, they were a part-and-parcel pair — they were often referred to in the same breath as just “Kendall and Kylie.” Even in those early days, though, Jenner was working a more classic style with neutral makeup.
Experimenting With Edge, 2015
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You could call this Jenner’s breakout year. She was booked solid with major modeling gigs, became a tabloid fixture, and started experimenting with her look. In this instance, she tried out a pair of long, wispy bangs that makes her look even more like her famous mother.
The ‘Clavi Cut’, 2016
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She’s tried extremely short chops and extra-long extensions, but there’s something to be said about this in-between sweet spot. Often called a “clavi cut” because of its collarbone-sweeping length, the hairstyle emphasizes Jenner’s long layers and waves.
Statement Color, 2017
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Now a Met Gala veteran, Jenner took the 2017 fundraiser as an opportunity to try out a fresh new look. She gave her hair the artfully dampened treatment, went for minimal eye makeup, and let her lips stand out with a crisp shade of bright crimson.
Getting Real, 2018
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Even world-class supermodels have insecurities. In 2018, Jenner made headlines when she opened up about her struggles with acne, telling Vogue, “I was trying to figure out for so long why my skin was breaking out. Was it hormones? Was it what I’m eating? Am I allergic to something? Am I using the wrong products?” For Jenner’s millions of fans, the vulnerability was both refreshing and relatable.
Pivot To Blonde, 2019
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Jenner’s actually gone blonde a few times over the years, but one of her best shades was this sandy, dimensional look from 2019. She colored her hair just ahead of New York Fashion Week Spring/Summer 2020, and it was incorporated into several of her best runway looks.
Caramel-Streaked Mid-Lengths, 2020
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Like most people, Jenner wasn’t too out-and-about in 2020. At the very beginning of the year, though, she served up enough beauty inspiration to get through the next several months when she debuted a fresh hair color: her usually deep brunette, but streaked with more caramel-colored pieces through her mid-lengths.
Simple Sophistication, 2021
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One thing about Jenner? She knows when to let her clothes do the talking, and adjusts her beauty look accordingly. At the 2021 Met Gala, she let all the focus stay on her jewel-encrusted ensemble, opting for a sleek yet simple updo and pared-down makeup.
Golden Ginger Hair, 2022
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It seemed like everyone was going red in fall 2022, and Jenner was leading the pack. She kept the long layers and curtain bangs she’d been enjoying for much of the year, but transformed it all with a vibrant, gold-toned ginger red that warmed up her entire look.
Y2K Influences, 2023
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She was pretty young through the early ‘00s, but that didn’t stop Jenner from incorporating several of the decade’s top trends into her looks through 2023. Here, she went for a Pamela Anderson-esque updo with a touch of brown lip liner to really lock in the vintage vibe.
Practically Platinum, 2024
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For her latest dalliance with blonde, Jenner went in a new direction: a bright, cool-toned, nearly platinum color. Debuted amid the Spring/Summer 2025 fashion month rollout, it’s already one of the year’s most talked-about celebrity beauty moments.