Kylie Jenner may be the youngest member of the Kardashian-Jenner clan, but she’s certainly carved out her own path since October 2007, when Keeping Up With the Kardashians premiered on E!
No longer known simply as the daughter of Kris and Caitlyn Jenner or the little sister of Kourtney, Khloé, Kim and Kendall, Kylie is a serious force to be reckoned with in her own right.
In March 2019, she became the world’s youngest “self-made billionaire” thanks to her uber-successful business ventures in makeup, with Kylie Cosmetics, and fashion, with Kendall + Kylie. (Although Forbes later revoked the title, estimating in May 2020 that she is actually worth just under $900 million.)
Further cementing Kylie’s place in history is her own spinoff series on E!, Life of Kylie, and her undeniable social media footprint. Kylie boasted more than 140 million followers on Instagram alone in August 2019, and as of July 2019, the multihyphenate was taking in a whopping $1.2 million per Instagram post.
The businesswoman has also managed to captivate the world with her personal life. Kylie has kept tongues wagging with high-profile relationships with rapper Tyga, whom she dated on-and-off from 2015 to 2017, and Travis Scott, whom she began dating in April of 2017. She went on to welcome her first child, daughter, Stormi Webster, with Scott in February 2018. They split in October 2019.
Prior to becoming a mom, she also had the world guessing about her pregnancy status, keeping mum even after Us Weekly confirmed her big news in September 2017.
Scroll down to relive the makeup mogul’s biggest moments through the years!
Kris gave birth to her youngest child — her second with ex Caitlyn — on August 10, 1997, completing her brood of six.
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At just 9 years old, Kylie became a household name after being thrust into the spotlight with the premiere of Keeping Up With the Kardashians. The family celebrated the show’s 16th season in March 2019.
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The TV personality made her big runway debut for designer Abbey Dawn at New York Fashion Week in September 2011.
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Kylie began a romance in March 2013 with Will Smith and Jada Pinkett Smith’s son Jaden, but the pair had cooled off by December. “I don’t have a boyfriend, but I do really want that boyfriend prom experience,” she told Seventeen Prom at the time. “If I couldn’t find a boyfriend, I would want to go with one of my best guy friends, like Jaden. I know I’d have fun with him – he makes me laugh and he is a great dancer.”
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2013 was a big year for Kylie: She got her start in fashion alongside big sis Kendall when the two collaborated with PacSun for their first clothing line.
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Kylie’s family and friends threw her a lavish sixteenth birthday party at Nobu in Malibu. In attendance at the bash were famous faces such as Kylie’s ex Jaden, Hailee Steinfeld, Tyga, Naya Rivera and Hailey Baldwin. Drake, Big Sean and The Weeknd also performed at the celebration.
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Just 18 days after her 16th birthday, the teenage Kylie crashed her Mercedes Benz in a three-car collision in Calabasas, California. Kylie kept her cool, however, with TMZ reporting that she apologized, asked those involved if they were OK and exchanged information.
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Kylie addressed her altered appearance multiple times in 2014. “These plastic surgery rumors hurt my feelings to be honest and are kinda insulting,” she tweeted in April. She also addressed her larger lips in October, telling Twitter followers, “How long are we gonna talk about this lip thing lmao. Let’s get a our lives together guys and talk about some important s–t. Just talk about something new at least. I’m bored.”
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Kylie made waves when she began dating then-25-year-old Tyga at just 17. Brother-in-law Kanye West confirmed the pair’s relationship in February 2015, telling Power 105.1’s The Breakfast Club, “I think [Tyga] got in early. I think he was smart.”
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A new boyfriend wasn’t the only change in the model’s life that year: She also purchased her first $2.7 million home in May of that year.
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After more than a year of speculation, the businesswoman finally copped to lip injections in a May 2015 episode of KUWTK. “I have temporary lip fillers, it’s just an insecurity of mine and it’s what I wanted to do,” she said.
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Kylie revealed in an interview in June 2015 that she was taking care of her own expenses. “My mom cut me off financially three years ago,” she said. “I pay for everything — my car, my gas, and food, as well as my clothes.”
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The reality star completed high school in July 2015 and encouraged her fans to do the same. “I finished school last week,” she tweeted at the time. “I know I never post on social media when I’m in class but that doesn’t mean I don’t encourage education! Because I do!”
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After dad Caitlyn came out as a transgender woman, the entrepreneur admitted she had known about her secret for years. “I mean, obviously I knew about it my whole life, but it was never admitted to and then it was all said and done,” she told Wonderland magazine in February 2016. “I honestly just wanted to not be lied to. I just wanted honesty and no secrets.”
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Following an insanely successful launch of her lip kits, the reality star embarked on a new adventure — a makeup line called Kylie Cosmetics in 2016.
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Despite multiple breakups, including a split in May 2016, Kylie and Tyga progressed their relationship in June 2016 when the rapper moved into her pad.
One year later, the twosome split for good: Tyga moved out in April 2017.
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After her breakup with Tyga, Kylie quickly moved on with boyfriend Scott. The couple were spotted getting cozy at Coachella in April 2017.
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Kylie, who never attended her own prom, made one lucky student named named Albert Ochoa’s dreams a reality when she accompanied him to his school dance in April 2017.
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E! announced that same month that the star was going solo with her own show titled, Life of Kylie. The series premiered on the network on August 6, 2017.
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Multiple sources confirmed to Us Weekly in September 2017 that Kylie was pregnant with her first child.
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Though she stayed mum throughout her entire pregnancy, Kylie revealed in a February 2018 YouTube video that she and Scott had welcomed a daughter, Stormi.
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Kylie covered the America’s Women Billionaires issue of Forbes magazine in July 2018, which valued her at $900 million and put her on track to be the “youngest-ever self-made billionaire” in history.
A bash built for a queen! Kylie rang in her 21st birthday surrounded by all of her sisters and her mom in August 2018. A source told Us Weekly that Scott spun songs at the party and “cuddled all night behind the DJ booth” with his love.
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Kylie’s world was rocked in February 2019 when her best friend Jordyn Woods was caught in a cheating scandal with her sister Khloé’s then-boyfriend, Tristan Thompson. Woods, who had been living with Kylie, moved out of her home days later.
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Less than a year after covering Forbes’ America’s Women Billionaire issue, Kylie officially achieved the title of the youngest-ever self-made billionaire. “[The recognition] feels really good,” she told the publication at the time. “That’s a nice pat on the back. … I work really hard.”
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Kylie filed a trademark for her own baby line in March 2019.
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A source told Us in July 2019 that Kylie and her beau had marriage on the brain. “Marriage isn’t important to Kylie, but it’s increasingly important to Travis,” the source said. “Travis is definitely into it. Kylie hasn’t expressed huge interest in getting married but they’ve talked about it a lot.”
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Us confirmed in October 2019 that Kylie and Scott called it quits. “Travis and I are on great terms and our main focus right now is Stormi,” she tweeted at the time. “Our friendship and our daughter is our priority.”
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In May 2020, Forbes revoked Kylie’s billionaire status, alleging that the makeup mogul and members of her team lied about sales and forged tax returns to “look even richer.” Forbes estimated that Kylie’s personal fortune is actually just under $900 million, with more than a third of her earnings coming from selling 51 percent of Kylie Cosmetics to Coty in 2019. She disputed the “Inside Kylie Jenner’s Web of Lies” report, tweeting, “I’ve never asked for any title or tried to lie my way there EVER. period.”
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Kylie and Stormi appeared on the cover of Vogue Czechoslovakia’s “Bedtime Story” issue in June 2020. The proud mom told her Instagram followers that she shot the photo “at home on my iphone” amid the COVID-19 pandemic.
Kylie, Scott and their daughter took a trip to Laguna Beach, California, in July 2020. A source told Us at the time that while the exes were “not putting pressure” on getting back together, they “love spending time together and parenting Stormi.”
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