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Left: Kylie Jenner in 2011 Right: Kylie Jenner in 2020

Kylie Jenner's transformation — her changing fashion and beauty looks throughout the years

The Kylie Cosmetics mogul is a certified trendsetter

Bryony Gooch
US Writer
July 11, 2024
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Kylie Jenner has been in the spotlight ever since she was little, thanks to being a member of American reality TV's first family, The Kardashians. Growing up on television meant that Kylie's transformation over the years has been heavily documented - and scrutinized.

Whether it's speculation about her having cosmetic surgery or tweakments, or the number of fans influenced by her makeup and fashion, Kylie's transformation has attracted a lot of attention - and influenced a lot of people as a result.

She said in an episode of the show on June 20: "It’s a miracle I still have confidence and can still look in the mirror and still think I'm pretty."

WATCH: Kylie Jenner wows fans with bright pink hair
The new look was a major throwback to 2014

"I hear nasty things about myself all the time," she said in a tearful confessional. "I think it's just after 10 years of hearing about it, it just gets exhausting."

She admitted it does affect her, as "people have been talking about my looks since I was 12 or 13, before I even got lip filler."

Kylie has perhaps been the most adventurous of her sisters when it comes to changing up her looks, as she's gone from blue hair and ombré looks to bleach blonde hair, while transforming her clothes from street style chic to quiet luxury chic.

Considering Kylie's openness about her insecurities and how she has changed her appearance, HELLO! looks back at her most influential fashion and beauty moments over the years.


LOS ANGELES, CA - NOVEMBER 14:  TV personality Kylie Jenner arrives at the Premiere of Summit Entertainment's "The Twilight Saga: Breaking Dawn - Part 1" at Nokia Theatre L.A. Live on November 14, 2011 in Los Angeles, California.  (Photo by Jason Merritt/Getty Images)© Jason Merritt

2011 - Teen queen

Kylie, aged 14, captured the early 2010s perfectly as she kept her look fresh in a white sheer shirt without sleeves and a nude waterfall style skirt, paired with open toe heels. She kept her makeup look natural, and her signature dark tresses rolled down her shoulders in waves.


LOS ANGELES, CA - DECEMBER 03:  Kylie Jenner attends KIIS FM's Jingle Ball 2012 at Nokia Theatre LA Live on December 3, 2012 in Los Angeles, California.  (Photo by Jason LaVeris/FilmMagic)© Jason LaVeris

2012 - Sleek hair

While previously Kylie wore her hair in waves, in 2012 she opted for sleek straight hair, paired with edgier looks - for example, this black leather mini skirt and black t-shirt.


LOS ANGELES, CA - NOVEMBER 24:  Television personality Kylie Jenner attends 2013 American Music Awards at Nokia Theatre L.A. Live on November 24, 2013 in Los Angeles, California.  (Photo by Frazer Harrison/AMA2013/FilmMagic)© Frazer Harrison/AMA2013

2013 - Chunky bangs and ombré

As she stepped into the spotlight, Kylie got playful with her looks, whether it was through opting for a bold dark lip, or changing up her hair with chunky bangs and an ombre. She kept it casual at the American Music Awards with a white shirt and black pants, letting her hair do all the talking.


LAS VEGAS, NV - MAY 18:  Model Kylie Jenner attends the 2014 Billboard Music Awards at the MGM Grand Garden Arena on May 18, 2014 in Las Vegas, Nevada.  (Photo by Frazer Harrison/Getty Images)© Frazer Harrison

2014 - King Kylie era begins

A fan favorite look, Kylie's bold blue balayage with a white lacy slip kicked off an era - the King Kylie era. Between the ages of 17 and 21, Kylie played a lot more with her looks - whether through dyeing her hair pink, purple or blonde, and changing up her style a lot more.


Kylie stuns in Balmain

2015 - Glitzy glam

As the Kardashian-Jenners appeared to team up with Olivier Rousteing's Balmain, Kylie opted for shimmering glam looks as she walked more and more red carpets. Often the dresses were figure-hugging with intricate cut-outs. Here, as she leans against the Balmain figurehead, she wears one of his intricate white cut-out dresses - and it looks iconic.


Kylie in her bleach blonde era

2016 - Bleach blonde

Kylie rocked long, bleach blonde hair as part of her King Kylie era, which stood out as she wore more casual fits, like a white oversized t-shirt cinched with a green corset and matching boots.


Kylie opts for casual athleisure

2017 - Form fitting looks

At 20 years old, Kylie emphasized her build with figure-hugging looks, whether through wearing more athleisure style outfits or tight fitting dresses.


Kylie kept it casual as she embraced motherhood

2018 - Natural look

As Kylie embraced motherhood, she opted for a more natural look, going back to her natural dark hair color, typically sporting a chignon, and simplifying her makeup looks. 


NEW YORK, NY - MAY 03:  Kylie Jenner is seen on May 3, 2019 in New York City.  (Photo by Gilbert Carrasquillo/GC Images)© Gilbert Carrasquillo

2019 - Kylie means business

As a young billionaire and mother, Kylie wore more serious looks in 2019 to show she meant business. A pinstriped, oversized blazer as a dress paired with glittering fishnets was the perfect office to dancefloor look - made even more iconic as she carried her daughter Stormi in it.


Kylie Jenner's colorful look

2020 - Stay-at-home chic

From the midst of the pandemic, Kylie sported a younger look than usual - a brightly colored top and honey blonde highlights - certainly a major change from her extravagant red carpet looks.


Kylie sports ultra long hair

2021 - Ultra-long hair

Kylie wore her dark tresses super long, past her waist, as she took a trip away. As she posed in a bikini, her hair touched her hips.


Kylie Jenner stuns in Dolce & Gabbana

2022 - Italian girl summer

Attending her sister Kourtney's wedding to Travis Barker, Kylie embraced the Dolce & Gabbana theme with a black figure-hugging dress and bold, fox-like eye makeup. 


PARIS, FRANCE - JANUARY 23: Kylie Jenner wears a Schiaparelli dress, outside Schiaparelli, during Paris Fashion Week - Menswear Fall-Winter 2023-2024, on January 23, 2023 in Paris, France. (Photo by Claudio Lavenia/Getty Images)© Claudio Lavenia

2023 - Lioness

Kylie certainly turned heads as she rocked up to Schiaparelli's Haute Couture runway wearing a piece straight out of the show - a strapless, figure-hugging dress with a giant lion's head on it. But fear not - the head wasn't real. Irina Shayk would go on to rock the same dress on the runway, but all eyes were on the cosmetics mogul.


PARIS, FRANCE - JANUARY 24: (EDITORIAL USE ONLY - For Non-Editorial use please seek approval from Fashion House) Kylie Jenner attends the Jean Paul Gaultier Haute Couture Spring/Summer 2024 show as part of Paris Fashion Week  on January 24, 2024 in Paris, France. (Photo by Pascal Le Segretain/Getty Images)© Pascal Le Segretain

2024 - Angelic glow

Not only has Kylie been wearing more natural makeup looks, but the biggest theme of her looks this year has been an angelic glow. She's worn a number of gorgeous, almost bridal champagne-toned gowns, with glowy cheeks and sultry natural hair.

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