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Kylie Jenner Then and Now: Reality star's transformation through the years

From 'KUWTK' to 'Kylie Cosmetics', Kylie Jenner has reinvented herself several times over
PUBLISHED SEP 12, 2023
Kylie Jenner through the years (Hayu/YouTube, Getty Images)
Kylie Jenner through the years (Hayu/YouTube, Getty Images)

Kylie Jenner, the reality star, entrepreneur and social media personality, over the years 

Kyline Jenner recently appeared in promotional campaigns for @acnestudio. (Instagram/@kyliejenner)
Kyline Jenner, the reality star, social media personality and entrepreneur (Kylie Jenner/Instagram)

American reality TV star, social media personality, entrepreneur and socialiate, Kylie Jenner, is undoubtedly one of the most popular and influential names in pop culture. Following her first apperance in 'Keeping Up with the Kardashians' back in 2007, Kylie has evolved under the spotlight from a 10-year-old child to a 26-year-old reality TV sensation, make-up mogul and a proud mother-of-two. Amid her ongoing romance rumors with Timothee Chalamet, here's a glimpse of the youngest Kardashian-Jenner sibling's transformation through the years. 

Kylie Jenner's career beginnings as a 10-year-old in 2007 

Kylie Jenner was just 10 years old when she first appeared on 'KUWTK'
Kylie Jenner was just 10 years old when she first appeared on 'KUWTK' (E! Entertainment)

Kylie Jenner was just 10 years old when she first appeared in the E! reality TV series ‘Keeping Up with the Kardashians’ with her parents and siblings. The success of the show resulted in the creation of several spin-offs like ‘Kourtney and Kim Take Miami’, ‘Khloe & Lamar’, ‘Kourtney and Kim Take New York’, and ‘Kourtney and Khloe Take The Hamptons’, which saw multiple guest appearances by Kylie, the youngest one among the Kardashian-Jenner siblings.

Kylie Jenner's early ventures: On the red carpet, hosting gigs and music videos between 2011 and 2014

Kendall and Kylie Jenner for 'Hunger Games' premiere (On Air With Ryan Seacrest/YouTube)
Kendall and Kylie Jenner for 'Hunger Games' premiere (On Air With Ryan Seacrest)

In August 2011, Kylie Jenner along with her sister Kendall, hosted ‘Glee: The 3D Concert Movie’ at the Regency Village Theater in Westwood, Los Angeles. That same year, they were selected as the "Style Ambassadors” of Seventeen Magazine after a feature on the publication’s ‘Style Stars of the Year.’ The Jenner sisters went on to host the premiere of ‘The Vow’ in Hollywood and interviewed ‘The Hunger Games’ cast at the film’s LA premiere in 2012. Kylie also appeared in an episode of ‘America’s Net Top Model’ alongside Kris Jenner and her sister Kendall in late 2012. This sisters went on to co-host the 2014 Much Music Video Awards before appearing in PartyNextDoor’s ‘Recognize’ music video in mid-2014. Kylie even appeared Jaden Smith's ‘Blue Ocean’ music video that same year.

The 'Kylie Jenner Challenge' and lip augmentation rumors in 2015

Kylie Jenner
Kylie Jenner admitted to getting lip fillers during a 2015 episode of 'KUWTK' (E! Entertainment)

The year 2015 started on a dull note for Kylie after she and Kendall was booed onstage while introducing their then brother-in-law Kanye West's performance at the Billboard Music Awards. However, the young reality star soon garnered publicity for her plumped-up lips. The drastic change in Kylie’s appearance also sparked speculation of the-then teenager’s use of lip fillers. In a May 2015 episode of ‘KUWTK’, Kylie admitted to getting "lip augmentation." Without any indication of Kylie using the method, the viral practice of suctioning one’s lips into a small glass to induce greater blood flow resulting in the swelling of lips was named the “Kylie Jenner Challenge.” Addressing the scrutiny around her lips, Kylie said, “I'm not here to try & encourage people/young girls to look like me or to think this is the way they should look,” as per The Hollywood Reporter.

Kylie Jenner confirmed relationship with Tyga at her 18th birthday in 2015

Kylie Jenner in Tyga's Dope'd Up music video (Tyga/YouTube)
Kylie Jenner in Tyga's Dope'd Up music video (Tyga/YouTube)

Kylie and Tyga first sparked romance rumors after the duo was spotted together at the former's 17th birthday party in 2014. This was shortly after Tyga's relationship with his fiance and baby mama, Blac Chyna, came to an end. Kylie and Tyga seemingly confirmed their relationship when the former turned 18 in 2015. According to Showbiz Cheatsheet, the rapper allegedly bought the newly adult Kylie a $320,000 Ferrari for her 18th birthday. The latter even appeared on two of Tyga's music videos, including 'Stimulated' and 'Dope'd Up.' The pair eventually parted ways in 2017. 

The birth of Kylie Cosmetics in 2016

Kylie Jenner for 'Kylie Cosmetics'
Kylie Jenner for 'Kylie Cosmetics' (Kylie Jenner/Instagram)

In August 2015, Kylie announced that she would be launching her first lipstick line as a part of her self-titled lip kit brand ‘Kylie Lip Kit.’  In February 2016, the name of her cosmetic company was changed to ‘Kylie Cosmetics’. After the renaming, the number of kits produced by the brand rose from an initial 15,000 to 500,000, per Forbes. In March 2016, Kylie released a three-minute-long promotional video for a series of lip glosses directed by Colin Tilley, starring models Karin Jinsui, Mara Teigen, and Jasmine Sanders.

The youngest person on Forbes 'Celebrity 100' list and 'Life of Kylie' in 2017

Kylie Jenner in a still from 'Life of Kylie' (Hayu/YouTube)
Kylie Jenner in a still from 'Life of Kylie' (Hayu)

In 2017, Kylie appeared at number 59 on Forbes ‘Celebrity 100,’ becoming the youngest person on the list at 19 years of age. The list reportedly names the 100 highest-paid celebrities of the previous 12 months. That same year, she also appeared in ‘Life of Kylie’, a reality show revolving around her life. In May 2018, Kylie collaborated with her mother, Kris Jenner, to launch Kris Cosmetics on the occasion of Mother’s Day. She went on to launch the second KKW x Kylie Cosmetics collection with her elder sister Kim Kardashian after their first collection came out in 2017. Kylie even introduced Kylie Cosmetics mobile app that year.

Kylie Jenner welcomes her first child with Travis Scott in 2018

SANTA MONICA, CALIFORNIA - AUGUST 27: Travis Scott and Kylie Jenner attend the Travis Scott:
Travis Scott and Kylie Jenner with their daughter Stormi at the 'Look Mom I Can Fly' premiere (Getty Images)

Following her break-up with Tyga, Kylie was seen with Travis Scott at Coachella 2017, sparking immediate romance rumors. Nearly a year later, Kylie welcomed her first child with the rapper, daughter Stormi, on February 1, 2018. The year 2018 also saw Kylie having a cameo appearance in Gary Ross’ heist comedy film ‘Ocean’s 8.’ The reality star appeared in the popular star-studded Met Gala scene of the movie along with her sisters, Kim and Kendall. While Kylie and Travis was rumored to have split in 2019, they quarantined together for the sake of their daughter and hopes of reconciling during the Covid-19 pandemic.

Kylie Jenner's 'youngest self-made billionaire' controversy in 2019

Kylie Jenner for her 21st birthday (Kylie Jenner/Instagram)
Kylie Jenner for her 21st birthday (Kylie Jenner/Instagram)

In 2019, Forbes dubbed Kylie the “world’s youngest self-made billionaire” at the age of 21. The magazine reportedly estimated that the Kylie Cosmetics founder’s net worth was US $1 billion at the time. However, Kylie’s “self-made billionaire” title sparked controversy as she was part of the privileged and well-connected Kardashian-Jenner clan. In May 2020, Forbes addressed the situation and accused Kylie of forging tax documents to make herself appear to be a billionaire.

Kylie Jenner launches 'Kylie Skin' in 2019 

Kylie Jenner for the launch of 'Kylie Skin' in 2019 (Kylie Jenner/Instagram)
Kylie Jenner for the launch of 'Kylie Skin' in 2019 (Kylie Jenner/Instagram)

In May 2019, Kylie founded her own skincare brand named ‘Kylie Skin’. She also went on to launch a third collaboration with her half-sister Khloe Kardashian called Kylie Cosmetics x Koko Kollection. In September 2019, Kylie revealed she was the makeup artistic director for Balmain's Spring 2020 runway show at Paris Fashion Week. She also teamed up with Balmain to launch a capsule makeup collection to celebrate their collaboration. This marked Kylie’s first collaborative venture outside her family circle.

Kylie Jenner's 'Rise and Shine' goes viral on TikTok

Kylie Jenner's viral
Kylie Jenner's viral 'Rise and Shine' clip originated from her October 2019 office tour video (Kylie Jenner/YouTube)

In October 2019, Kylie filed to trademark the phrase “rise and shine,” which eventually became a meme after a clip of the reality star singing the phrase to her daughter went viral. The #RiseandShine hashtag became TikTok’s fastest-growing hashtag trend. Meanwhile, Kylie also filed to trademark the phrase "riiise and shiiinnee." Both the phrases reportedly covered cosmetics and clothing, respectively.

Kylie Jenner's entrepreneurial journey through 2020

Kylie Jenner and Stormi Webster for 'The Stormi Collection' 2020 (Kylie Jenner/Instagram)
Kylie Jenner and Stormi Webster for 'The Stormi Collection' 2020 (Kylie Jenner/Instagram)

In January 2020, Kylie announced that she trademarked Kylie Con, Kylie Kon, and Kylie Museum. On February 1, 2020, she released a Valentine's Day Collection named ‘The Stormi Collection’, to mark her daughter’s birthday. Meanwhile, Kylie also made a cameo appearance on Ariana Grande and Justin Bieber's ‘Stuck with U’ music video in May 2020. In June 2020, Kylie teamed up with Kendall to launch Kylie Cosmetics x Kendall Jenner collection. In August 2020, she launched the ‘Summer Sailor Collection’, the first-ever false lashes from Kylie. The entrepreneur also made a cameo in Cardi B and Megan Thee Stallion’s ‘WAP’ music video that same month. Kylie reportedly held the top position of Forbes’ list of highest paid celebrities in 2020.

'Keeping Up With the Kardashians' finale and launch of Kylie Swim in 2021

Kylie Jenner for 'KUWTK reunion' after the finale of 'KUWTK'
Kylie Jenner for 'KUWTK reunion' after the finale of 'KUWTK' (Kylie Jenner/Instagram) 

In 2021, Kylie and the Kardashian-Jenner family announced that their popular reality show 'Keeping Up With the Kardashians' would come to an end after 20 seasons and nearly 15 years. In September 2021, Kylie launched 'Kylie Swim', a new swimwear line for women of all sizes. However, the release was met with immense backlash as consumers claimed that the product failed to meet quality standards. That same month, Kylie announced the release of a new line for babies called 'Kylie Baby'.

Kylie Jenner becomes the first woman to gain 300 million followers on Instagram in 2022

Kylie Jenner's post from January 2020, a few days after she reached 300 million on Instagram
Kylie Jenner's post from January 2020, a few days after she reached 300 million on Instagram (Kylie Jenner/Instagram)

In January 2020, Kylie made history as the first woman to gain 300 million followers on Instagram surpassing previous recordholder Ariana, as per People. At the time, football star Christiano Ronaldo held the record of the most-followed account with 389 million followers. At the time of writing, Kylie Jenner boasts 399 million followers. 

Kylie Jenner's return to television with 'The Kardashians'

Kylie Jenner for 'The Kardashians' premiere (Kylie Jenner/Instagram)
Kylie Jenner for 'The Kardashians' premiere (Kylie Jenner/Instagram)

In April 2022, Kylie returned to television with her family members in the new Hulu reality series 'The Kardashians'. The show featured Kris Jenner, the Kardashian-Jenner sisters as well as their former and current partners, including a guest appearance by Kanye. The first season of the show premiered on April 14, 2022 while second season premiered on September 22, 2022. The series was renewed for the third season and officially aired on May 25, 2023.

Kylie Jenner welcomes her second child with Travis Scott in 2022

Kylie Jenner with her son Aire Webster
Kylie Jenner with her son Aire Webster (Kylie Jenner/Instagram)

In addition to her professional life, Kylie also continued to make news for her on-and-off relationship with Travis. Kylie first announced she was expecting her second child with the rapper on September 27, 2021. The socialite gave birth to her second child, son Aire, on February 2, 2022. However, on Janaury 2023, a source told People that Kylie and Travis had finally parted ways and that Kylie was focusing on her "kids and business."

Kylie Jenner addresses plastic surgery rumors on 'The Kardashians' in 2023 

Kylie Jenner admits to getting a boob job done during an episode of 'The Kardashians' (Keeping Up With The Kardashians/YouTube)
Kylie Jenner admits to getting a boob job done during an episode of 'The Kardashians' (Keeping Up With The Kardashians/YouTube)

Kylie Jenner's changing appearance has long been a subject of speculation among social media users. The reality star was also been accused of having numerous plastic surgeries. Back in 2015, she denied surgery rumors during a Cosmopolitan interview, saying, "You guys have watched me grow up since I was 9. My face is going to get different. Now, I know how to do my makeup, contour, and everything. I’m not against surgery. I’d never say no, but I don’t desire it right now." However, during an episode of the third season of 'The Kardashians' in July 2023, Kylie admitted to have gone under the knife to get her "breasts done" before welcoming her first child. "I just wish, obviously, I never got them done to begin with. I would recommend anyone who is thinking about it to wait until after children,” she reportedly said, as per Los Angeles Times.

Kylie Jenner sparks relationship rumors with Timothee Chalamet 

Kylie Jenner, Timothee Chalamet and Laverne Cox at US Open 2023 (@usopen/Twitter)
Kylie Jenner, Timothee Chalamet and Laverne Cox at US Open 2023 (@usopen/Twitter)

Kylie reportedly met Timothee the first time when they attended the Jean Paul Gaultier fashion show in January 2023 during Paris Couture Week, as per Harper's Bazaar. Romance rumors began to swirl but the pair remained tight-lipped about their relationship. The duo were pictured together for the first time at Timothee's Beverly Hills home in June. Earlier this month, the duo made their public appearance together at Beyonce’s star-studded birthday concert. On Sunday, September 10, Kylie and Timothee packed on  the PDA while attending the US Open men’s singles finals.

Kylie Jenner x Acne Studios

Kylie Jenner for Acne Studios (Kylie Jenner/Instagram)
Kylie Jenner for Acne Studios (Kylie Jenner/Instagram)

As per Kylie's latest social media activity, the 26-year-old has teamed up with Acne Studios for their FW23 denim collection. The reality star and entrepreneur took to Instagram to share several photos and videos from her new ad campaign appearance. The most recent post on Kylie's Instagram, at the time of writing, is a behind-the-scenes sneak peek into Kylie Jenner x Acne Studios shoot. Kylie is also set to appear in the fourth season of 'The Kardashians.'

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