Kylie Jenner’s Style Evolution

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.

Kylie Jenner looked adorable in a baby-doll style top and white shorts while attending a benefit event in 2008.

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.

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.

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.

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!

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.

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!

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.

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”.

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.

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.

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.

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.

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.

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.

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.

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.

A vision in a strapless red satin gown, Kylie Jenner put her best leg forward at a pre-Grammy’s event in 2019.

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!