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Kylie Jenner Then and Now: 11 Photos of Her Dramatic Fashion Evolution Through the Years

kylie jenners fashion transformation
Source: MEGA

Sep. 25 2023, Published 8:05 a.m. ET

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2012

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Kylie Jenner scored the Youngest Self-Made Billionaire title when she reached the $1 billion mark when she was 21.

Before finding her style, Kylie Jenner donned a simple all-black outfit during a date with Cody Simpson. The pair started dating after they met at the Breaking Dawn: Part 1 premiere in November 2011.

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2014

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She considers Lady Gaga as her role model.

The Kylie Cosmetics founder rocked her denim jacket, complemented with black boots and pants as she spent some time with her friends in Beverly Hills, Calif.

2015

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She also wanted to become a model.

Jenner, who started dating Timotheé Chalamet this year, turned people's heads when she wore a gray, backless dress and black cage heels during a lunch at Sugarfish Sushi in Calabasas, Calif.

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2016

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Kylie Jenner has been a staple in the reality TV world.

Jenner started exploring the fashion world before launching her The Kylie Shop in December 2016.

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2017

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She underwent surgery when she was a kid, leaving her with a large scar on her left leg.

Jenner arrived at the Marie Claire's Image Maker Awards 2017 in West Hollywood, Calif., sporting a purple Balmain dress with thigh-high cutouts.

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2018

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Her Kylie Cosmetics brand started as the Kylie Lip Kit.

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The Keeping Up With the Kardashians alum set people's pulses racing when she wore an all-black, skintight leather cropped top and high-waisted pants. She also ditched her signature black hair and debuted her blonde locks instead.

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2019

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She has a massive car collection.

Jenner explored her wardrobe and arrived at the Met Gala after-party in a jaw-dropping aqua-green mermaid-inspired dress and a matching wig. At that time, he was still dating rapper Travis Scott, whom she broke up with in January 2023 after five years of on-again, off-again relationship.

The pair shares daughter Stormi and son Aire.

"Kylie and Travis are off again, they were supposed to spend the holidays together, but she went to Aspen to be with her family and friends up there," a source told Us Weekly. "This has happened so many times before, they're known to be on again off again, but always remain friends and great co-parents."

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2020

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She launched her own reality show, 'Life of Kylie.'

She let her blue and black dress hug her curvy, hourglass figure as she posed for photographers at the 2020 Vanity Fair Oscar Party.

Jenner revealed on Instagram that the dress gave her some trouble, writing, "couldn't really sit in this but it was worth it."

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2021

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She holds multiple Guinness World Records.

Jenner went out with her daughter Stormi for lunch during a break from New York Fashion Week. She rocked her autumn look, which included a brown leather jacket-turned-minidress and animal-printed knee-high boots. She completed her ensemble with her furry bucket hat.

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2022

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Kylie Jenner collaborated with her sister, Kendall Jenner, to create the clothing brand Kendall + Kylie.

The makeup mogul graced the Schiaparelli show during Paris Fashion Week at White & Case LLP in Place Vendome with her beauty while wearing a blue velvet dress that featured a plunging neckline. She stole the show with her outfit paired with her black and gold heels.

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2023

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She also has a fragrance line.

Jenner did it again at the 2023 Schiaparelli fashion show in Paris when she wore a black dress and held a massive faux lion's head.

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