As of November 3, Kendall Jenner will officially be able to drink. (Raise your hand if you feel old.) To help toast her into her 21st year, we're taking a look at Jenner's best beauty moments from her career, which, we should note, began when many of us were just entering middle school.
In the decade since Keeping Up with the Kardashians premiered, Jenner has gone from a shy big sister to a bona fide star in her own right. Just this fall, she's appeared on not one, but five Vogue covers. She's one of the top 10 most followed celebrities on Instagram. And business isn't slowing down anytime soon — she's currently prepping for the 2016 Victoria's Secret Fashion Show next month.
And yet, despite being in the Kardashian world, Jenner has never quite been of the Kardashian world. She told Vogue, "I’ve always been super-different from all my sisters, especially my Kardashian sisters. They’ve always been into the glam thing and dressing up every day and being in the thick of it."
Instead, Jenner tends to stick to classic looks that complement her features. If there's a wild beauty moment, such as those iconic bleached eyebrows or sleek pixie, it's usually in the name of fashion. And if you're looking for an awkward phase, move right along, my friends.
Ahead, check out Jenner's 21 best beauty moments.
We only wish our middle school pictures looked this polished. At an event in 2008, Jenner wore a fresh face, loose waves, and braces.
Photo: Courtesy of Getty.
A year later, she started experimenting with makeup. Just like us, that consisted of heavy black liner and lip gloss. Jenner recently wrote on her website, "I went through a phase in middle school in which I'd wear a ton of black eyeshadow and liner. Sometimes, I would just layer on the eyeliner on the bottom lid." You and us both, sister.
Photo: Courtesy of Getty.
At the ESPYs in 2009, Jenner got her first big haircut — including long, choppy layers. Her hair was slightly crimped, a style that's actually back in vogue.
Photo: Courtesy of Getty.
Jenner opted for a low-slung side bun at the 2009 Teen Choice Awards. Long, piece-y bangs and gold shadow in her inner eye corners completed the early-aughts look.
Photo: Courtesy of Getty.
In 2010, she premiered what would soon become her signature: a simple, centre-parted blowout and barely-there makeup.
Photo: Courtesy of Getty.
Another one of Jenner's go-tos? The humble ponytail. She wore her first red-carpet version in 2011 at the premiere of Beastly.
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But things got a bit more edgy at the Teen Choice Awards in 2011, where Jenner braided her hair into a mini-fauxhawk and swept deep-burgundy shadow on her lids. We see you, Kenny.
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Jenner's lengthy fishtail braid was the stuff of Pinterest dreams at the Twilight: Breaking Dawn premiere in 2011.
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In 2012, Jenner tried glossy curls on for size. And can we take a moment to appreciate how great her eyebrows have looked from the very beginning? We're kind of mad about it, not gonna lie.
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At 16, Jenner wore a romantic updo worthy of the prom she skipped. Her face-framing layers are accented by sweet red lips.
Photo: Courtesy of Getty.
The 2013 American Music Awards saw a more dramatic — dare we say, Kardashian — version of Jenner. Always one to keep it classic, Jenner stuck to the centre-parted blowout, but this time with sleek strands and glossy eyes and lips.
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Jenner was French-girl-chic at the 2014 Fashion Media Awards. Burgundy, matte lips give an edge to her ballerina bun.
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At the 2014 Teen Choice Awards, Jenner went for the "wet hair" look, a trend her older sisters know well.
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At the 2014 Billboard Music Awards, she smouldered with allover brown shadow and pale nude lips.
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Peach gloss, shimmery-brown smoky eyes, and an easy updo: Jenner had her beauty look down, just in time for her big debut as the face of Estée Lauder.
Photo: Courtesy of Getty.
After the Victoria's Secret Fashion Show in 2015, Jenner wore a tiny half-topknot — and mile-long lashes left over from the catwalk.
Photo: Courtesy of Getty.
In 2016, Jenner went for a chop so dramatic, many people didn't even believe it was real.
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She kept the cuts (and faux cuts) coming, sporting a set of shaggy bangs and a loose updo later that year.
Photo: Courtesy of Getty.
We fell in love with Jenner's slick pixie at the Givenchy fashion show. While it was definitely faux, the look proved that she slays in pretty much any style she chooses.
Photo: Courtesy of Getty.
The ponytail returned at the 2016 Cannes Film Festival. This time, it was teased, full, and a tad more dramatic.
Photo: Courtesy of Getty.
Backstage at New York Fashion Week in September, Jenner wore a romantic side-part with pretty, side-swept bangs. As per usual, her makeup was understated and absolutely lovely.
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