From her early days as a goofy twin in the Kardashian clan to a self-made billionaire and young mom — Kylie Jenner’s had one heck of a journey — and we’ve watched it all play out on reality TV. So sit back and get ready for some serious pastel-hair moments, as we take you through the style evolution of everyone’s favourite Kardashian to watch!
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Kylie Jenner poses with sister Kendall at the KUWTK viewing party in 2007
The youngest of the Kardashian clan, Kylie Jenner was just 13 years old when she attended the viewing party for the families’ reality show, Keeping Up with the Kardashians. Kylie looked adorable — and very age-appropriate — in a pastel pink dress with a cute half-up hairstyle.
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Kylie Jenner gets used to celebrity appearances at a benefit in 2008
Kylie Jenner looked adorable in a baby-doll style top and white shorts while attending a benefit event in 2008.
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Kylie Jenner tries out bangs for an appearance in 2009
Attending an event for Wango Tango in 2009, Kylie Jenner stepped out sporting blunt bangs and a tank top with a tiered mini-skirt and flat sandals. The outfit was a miss and Kylie’s cute face was overwhelmed by those thick bangs — this may have been one of the few times where the youngest Jenner’s hair wasn’t an instant hit.
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Kylie Jenner rocks a blazer for a Wango Tango event in 2010
Sporting a floaty mini dress with a blazer worn over top, it’s clear Kylie Kardashian was beginning to consider current trends in her style choices and looking to try out more “mature” looks than we’d seen up to that point.
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Kylie Jenner channels her big sisters’ style for her outfit to a premiere in 2010
Looking like she fell right out of her big sisters’ closet, Kylie Jenner attended the 2010 premiere for Burlesque and had us doing a double-take. Looking like a bit of an awkward mess, the petite reality TV star looked overwhelmed by “trendy” pieces. From her suede-look ruched dress, wide waist-belt and caged booties to her severe makeup and too-tight slicked-back hair — it was all too much.
Related: JLo’s style evolution.
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Kylie Jenner nails it at a movie premiere in 2011
An early-favourite of ours, Kylie Jenner was perfection when she stepped out for the Twilight: Breaking Dawn premiere in Los Angeles in 2011. From the blush-pink floaty top and skirt to her t-strap pumps — down to her hair and makeup — it all worked!
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Kylie Jenner rocks bold red to a film premiere in 2012
For the premiere of The Vow, Kylie Jenner stepped out in a bold red mini dress with cut-out details and muted nude platform pumps.
Related: Celine Dion’s style evolution.
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Kylie Jenner is one (perfect) shade of grey at a film premiere in 2013
At the 2013 Hunger Games premiere, Kylie Jenner left us hungry for more of these style moments. Jenner nailed the look in a fitted grey midi-dress and booties, bold lip and perfect bombshell hair – yes, girl!
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Kylie Jenner begins her style transformation in 2014
Blink and you might have missed her. Kylie Jenner was almost unrecognizable at the 2014 Billboard Music Awards. Rocking a shorter hair style with bold blue highlights, a fitted, white strappy midi dress and super sexy lace-up pumps, it was clear the youngest Kardashian was definitely all grown up.
Related: Mariah Carey’s style evolution.
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Kylie Jenner shows major leg at the AMA’s in 2014
Looking like a star, Kylie Jenner stepped out and stepped up her red-carpet style game at the American Music Awards in 2014. Growing more popular by the day, 2014 (and 2015) would be the years that Time Magazine would name the Jenner sister’s “the most influential teens in the world”.
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Kylie Jenner begins to build an empire – and becomes a hair colour chameleon – in 2015
In 2015, Kylie Jenner launched the first release of Kylie Lip Kits, the beauty line that would eventually become the best-selling brand, Kylie Cosmetics. With a hit TV show and newfound style-star status, the young entrepreneur was definitely serving up her best looks — and making her biggest moves — yet.
Related: Jennifer Aniston’s style evolution.
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Kylie Jenner keeps it short and sweet at a launch party in 2016
2016 was the year of extravagant trips with her then-bff Jordyn Woods and red carpet coupling with then-boyfriend Tyga. It was also the year we discovered that Kylie Jenner had a serious “thing” for second-skin mini dresses — and some seriously killer curves to go with it.
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Kylie Jenner is a goddess at the MET Gala in 2016
Statuesque in a custom, silver Balmain gown and sporting a sleek, cropped hair style, Kylie Jenner was absolute perfection at the 2016 MET gala. Jenner would later reveal that she suffered for her style that night, as her gown left her with bloody scratches along her legs and her uncomfortable choice in shoes left her feet swollen and purple — no pain, no gain Kylie — as the look landed her on “best-dressed” lists everywhere.
Related: Selena Gomez’ style evolution.
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Kylie Jenner is a vision in custom Versace for the MET gala in 2017
Kylie Jenner stepped out with a bold and cropped platinum-blonde ‘do and custom Versace gown for the 2017 MET gala and absolutely stole the show.
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Kylie Jenner is a boss — and dresses the part – at the MTV Video Music Awards in 2018
Looking every bit like a boss on her way to making billions, Kylie Jenner rocked a white blazer-style dress and slicked-back blonde locks to the 2018 MTV Video Music Awards. The look was clean, sexy and on-trend and it still ranks as one of our favourites.
Related: Angelina Jolie’s style evolution.
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Kylie Jenner and Travis Scott rock the red carpet at the MET gala in 2018
2018 was the year of stylish couples’ outfits between Kylie Jenner and rapper Travis Scott. More importantly, it was the year of Stormi — the couples’ baby, who would be born just a few months before this show-stopping MET gala moment.
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Kylie Jenner is a mermaid goddess at the MET gala in 2019
Giving us serious mermaid vibes, Kylie Jenner knocked it out of the park at the 2019 MET gala, serving up pastel-purple hair and a sequin-mesh gown with feather accents.
Related: Zoe Kravtiz style evolution.
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Kylie Jenner is pretty in pink at the Grammy’s in 2019
Love or hate this one, you cannot deny it was a serious style moment. With so much to look at, the stunning Kylie Jenner still shone through and absolutely served this one on the Grammy’s red carpet in 2019.
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Kylie Jenner is a vision in red at a pre-Grammy’s event in 2019
A vision in a strapless red satin gown, Kylie Jenner put her best leg forward at a pre-Grammy’s event in 2019.
Related: Lady Gaga’s style evolution.
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Kylie Jenner only gets better at the Vanity Fair Oscar Party in 2020
Kylie Jenner stole the show in this silver-and-navy Ralph and Russo dress for the Vanity Fair Oscar Party in 2020 — her first of two killer looks that evening. If this 2020 look was any indication of what’s to come in 2021 — we’re all in, Kylie!