Kylie the Konqueror: How Kylie Jenner overcame her insecurities and took over the world

Kylie Jenner's baby, Stormi is taking over social media right now. Her cute face is everywhere and so is her mama's for the right reasons, but it wasn't always so.

                            Kylie the Konqueror: How Kylie Jenner overcame her insecurities and took over the world
Kylie Jenner (Source : Getty Images)

Kylie Jenner's baby Stormi is nine weeks old now and her relationship with boyfriend Travis Scott seems stronger than ever. She's built herself a lipstick empire and is just getting more famous by the day on social media.

But Kylie, unlike the rest of the Kardashians/Jenners, is perhaps the one member of the clan, who has always craved for a different life, a place where she can be herself and not feel the pressures that being the star that she is, brings.

It's almost as though underneath the expensive falsies and kissproof lip kits, 20-year-old Kylie Jenner is just like the rest of us - she has similar insecurities, relationship drama, and the aspiration to be just like her older, seemingly cooler siblings. 


Kylie, born to then Summer Olympics decathlon winner Bruce Jenner (who is Caitlyn Jenner now) and the Kardashian momager Kris Jenner. But though she was born in one of the fanciest families today, she didn't have a Gossip Girl type life.

She was more of the Serena Van Der Woodsen than the Blair Waldorfs of the world. She was homeschooled until high school and never got to go to prom and was extremely insecure about her features like any teenager would be. It was perhaps just 10 times worse for her, as the family show 'Keeping Up With The Kardashians' gained popularity and she found herself under the constant scrutiny of the whole world. 


People were talking about her and though her fan following was growing, so were the constant hate comments. They made her so insecure that at the age of 14 she started showing up at awards with heavily-lined eyes and thick falsies, possibly trying to draw attention away from her "thin" lips she's always been insecure about. But as she grew more popular, her lips grew bigger.

By May 2014, Kylie had already started overlining her lips and you can see that she was playing around with lip fillers at the time. In November the same year is when she became the face that we know today - thickly painted, pouty lips, making her almost unrecognizable. 

The evolution of Kylie's lips - 2008, 2011,2014 (Getty Images)


Kylie has opened up about feeling like she's the ugliest of the family and how she thought no boy would ever want to kiss her because of her thin lips. In an episode with KUWTK she confesses, "I have temporary lip fillers, it's just an insecurity of mine and it's what I wanted to do. I'm just not ready to talk to reporters about my lips yet because everyone always picks us apart." Her words sound true because they are. It's like you can almost hear the younger Kylie, probably bawling her eyes out because she felt so inadequate. 

Kylie sports bangs at the 2015 MTV VMAs (Getty Images)


Soon after, she appeared at the MTV Video Music Awards in 2015 and looked curvier than expected, leading to speculation that she had more work done on herself than just her plump lips. She denied accusations that she'd gone under the knife and added some butt implants along with some waist trimming procedures, but her petite waist and the largely rounded backside screamed otherwise. But even if she did do it, it wouldn't be a surprise. 

Her Teen Vogue interview from the same year is what would make you think so. She revealed how much being a social media star had affected her. She said, "Today, I posted my Instagram picture three different times. I kept deleting it and re-posting it because I kept looking at the comments and they were bad comments. And I was like, 'Ahhh!' and I kept re-posting it. The people who take the time to write these comments are so mean and hateful, like they just want to come at you and hurt you."

She also admitted, "I feel like I've heard the worst anyone can say about me over and over every day. So it's like my self-esteem definitely wasn't good at a point, I guess?" Keeping up with Kylie has been fairly easy thanks to her Instagram, but it looked like she hadn't been able to keep up with herself at this point. 


In 2017, on Life of Kylie, she opened up about a therapy session she took because of how insecure she was about the way she looked. "I was 15 and I was insecure about my lips. I had really small lips," she said. She also revealed that she took a comment from a young boy who told her she'd never be a good kisser with those lips "really hard". "When a guy you like says that, I don't know it just really affected me. I just didn't feel desirable or pretty. I really wanted bigger lips. I ended up getting my lips done. It sticks with you," she said. 


The way she saw herself probably had a lot to do with the way Kris, their momager managed them. She's known to be a cutthroat businesswoman, after all, she really is the brains behind KUWTK. Though she did a stellar job as their manager, it may have made a young Kylie feel like a product that wasn't good enough to be marketed. When you grow up in a family that sells their private life on tape to make money, you are bound to want to grow up and be like them.But almost as if it were a miracle - Kylie turned her worst insecurities into a makeup empire. Around 2016, on the occasion of her birthday, Kylie decided to delight fans with the launch of Kylie Lip Kits in three shades. It had a lipliner and a liquid lipstick and cost $29 dollars. They sold out within a minute. Soon, Kylie Cosmetics was born - kylighters, eyeshadows, brushes, concealers, blushes and a wide range of lipsticks.

The company is worth $420 million and will be well over $1billion if it continues to grow the same way, by the year 2022. In just 18 months, Kylie went from being one of the rich sisters to the highest earning one, earning $18 million. From being a kid insecure about her lips - here she was selling lipstick. 

She also launched a nail color line called King Kylie with the brand Sinful Colors. The same year, Kylie teamed up with Kendall to start their own fashion line, which they launched at the NYFW. Though the line has been accused of cultural appropriation, stealing designs, imitating the black culture and more recently using Tupac Shakur's photograph without permission of the photographer Michael Miller who said they "misappropriated and wrongfully exploited" his art. 

than being sweepingly successful in business, her personal life has looked up too. She's found love with rapper Travis Scott, after her rollercoaster relationship with Tyga. She's got a beautiful daughter, Stormi Webster, who is already worth $3million, by the way.


Even with her pregnancy, she tried to keep it such a secret because she was scared of the response the baby would get - and rightfully so. The whole nine months, that she went under the radar, posting old pictures and hiding from paparazzi, she was trying to protect her child and herself from going back to a darker place perhaps. But it was when the baby video came out, that you could see how much Kylie Jenner had matured. She was far from an insecure teenager, she was a mature woman who understood the sharp pain of fame and knew how to use it for her benefit. 

It's like she said in an earlier episode of Life of Kylie, "I’m trying to not grow up too fast. I love my age. I love my fans. I love that we’re all young — the new generation. I want to make mistakes. I want to make bad decisions and learn from them. That’s the only way I’m going to grow."