Kylie Jenner’s Dramatic Transformation Is Turning Heads
18th March 2021

In the decade that Keeping Up with the Kardashians has been on the air, viewers have watched Kim, Kourtney, Khloé, Kendall, and Kylie undergo dramatic beauty transformations. The oldest of the bunch, Kourtney appears to be aging in reverse, thanks to her strict workout regime and organic, dairy-free, keto diet (via Elle). Kim famously overhauled her wardrobe, aided by her husband, Kanye West, according to People. Khloé famously shed weight, debuted her new “revenge body,” and sparked plastic surgery rumors as a result of her ongoing love affair with Facetune (via Us Weekly). Kendall morphed from a red carpet cutie into a bona fide supermodel. And then there’s Kylie Jenner. 

The youngest of the Jenner-Kardashian clan, Kylie has arguably flaunted the most dramatic beauty transformation of all. Because she was just 10 years old when Keeping Up with the Kardashians first aired, fans have truly gotten to see her grow up in the spotlight. From her famously over-lined pout to her collection of ever-changing wigs, this beauty entrepreneur isn’t afraid to make a statement. So, in honor of the reality show’s final season, let’s take a look at how much Stormi’s mom has transformed over the years.

Kylie became a front-row fixture at Fashion Week

Back when Keeping Up with the Kardashians first hit E!, Kylie Jenner was just a fresh-faced ten-year-old with a penchant for wearing pink on the red carpet. However, as the show progressed, so did Kylie’s killer sense of style. As a teenager, she debuted edgy looks with the confidence of a seasoned fashionista, even occasionally honing her skills on the catwalk. As MTV News reported, she made her New York Fashion Week debut in 2015, walking in rapper-turned-designer Kanye West’s Yeezy fashion show. With big sisters Kim Kardashian and Kendall Jenner leading the way, it didn’t take long before Kylie was soon a fixture at high-fashion events. 

According to E! News, she and ex-boyfriend Tyga made the rounds at NYFW 2016, sitting front row at the Alexander Wang show. She was also spotted at the Prabal Gurung show that week. In 2018, she and then-beau Travis Scott had a double date with Kim and Kanye West at the Louis Vuitton Show during Paris Fashion Week (via E! News). Not too shabby! 

Kylie also scored a coveted invite to the Met Gala in 2016, where she stunned in a semi-sheer, beaded Balmain gown, per Entertainment Tonight. Following her debut at fashion’s biggest night, she rocked a series of increasingly daring looks, keeping us guessing about her wardrobe up until the last minute.

Kylie experimented with wigs

While Kylie Jenner’s fashion evolution has been a whirlwind, so has her beauty game. At this point, the reality star’s love for brightly-colored wigs is well documented; however, the height of her wig craze really hit around 2016. It all started when the 16-year-old dyed her hair without the permission of her mom, Kris Jenner. As Kylie explained on her now-defunct website, “After that, I’ve just had this addiction to changing my hair. It makes me feel like a new person. I love feeling different and I love leaving the house knowing that nobody has ever seen me this way” (via People). Given this mentality, it’s no wonder Kylie has worn wigs in pretty much every color of the rainbow – teal, yellow, purple, pink, red, you name it!

Kylie also wasn’t shy about claiming wigs as her trademark. In 2016, she sparked controversy by boasting to Marie Claire, saying, “I started wigs, and now everyone is wearing wigs … I just do whatever I want to do, and people will follow.” Unsurprisingly, readers took offense to the celeb’s stance. Maybe that’s part of the reason why Kylie appears to have cooled her wig obsession in recent years.

Kylie turned her biggest insecurity into a billion-dollar business

Despite her riches and fame, Kylie Jenner was like any other teenager in that she struggled with insecurities. In her case, it was her less-than-plump pout. “I was super insecure about my lips,” the beauty mogul told Glamour in 2018. “I really wanted the illusion of bigger lips, so I overlined mine like crazy, and then people started getting obsessed.” She came clean about her decision to get lip injections in 2017 on an episode of Life of Kylie, telling viewers how a guy she’d once kissed remarked on her small lips (via Teen Vogue). But Kylie didn’t just stop at lip injections. 

According to Women’s Wear Daily, she officially launched her lip kits in late 2015, allowing makeup lovers to achieve their desired pout without fillers. The monster success of her lip kits on Instagram soon prompted her to expand into brick-and-mortar retail, which also proved highly lucrative. Two years after launching the business, Kylie told WWD that the brand earned $420 million in just 18 months since its launch.

As of this writing, Kylie Cosmetics has hit the $1 billion mark, powering the beauty mogul to expand her empire into skincare with the launch of Kylie Skin (via WWD). More importantly however, Kylie’s lip kits have cemented her place in pop culture history, making her name synonymous with a full, plump pout.

Kylie struggled with "ups and downs" after giving birth to her daughter Stormi

From cheating scandals to televised weddings, we’ve pretty much seen it all on Keeping Up With The Kardashians. However, Kylie Jenner managed to keep her 2018 pregnancy completely under wraps. After giving birth, Kylie opened up to Vogue Australia about why she’d chosen to keep those nine months such a secret. “I just knew that it would be better for me, and I could enjoy the whole experience if I did it privately,” she explained. “I just felt like it was a sacred special moment and I wasn’t ready to share it with everybody.”

After she had Stormi, Kylie spoke candidly about dealing with the “ups and downs” in a 2019 Instagram post. She also urged fans to be gentle with themselves. Perhaps this had something to do with the fact that the new mom was still coming to terms with her changing body shape. Although she admitted she “bounced back super fast” following the birth of her daughter, Kylie also made it clear she wasn’t putting pressure on herself to look the same way she did before getting pregnant. Instead, having a baby reinforced the importance of self-love for Kylie.

“I feel like having a daughter, and thinking about beauty in the future, has definitely changed me, and I feel like it has made me love myself more and accept everything about me,” she told Vogue Australia.

Kylie continues to set new trends

Just like her fellow Kardashian and Jenner sisters, Kylie holds a serious amount of cultural sway. From rocking bodycon dresses to runway-ready athleisure, she is a true trendsetter. And her newest obsession is … upside-down bikinis?

In February 2021, the New York Post reported that the reality star got behind the upside-down bikini craze, which, as the name suggests, turns the traditional way to wear a two-piece upside down. Though the trend was first popularized in 2018, Kylie pushed for its revival after flaunting the body-baring look on Instagram. Naturally, she didn’t pass up the chance to plug her Kylie Skin products in the process — momager Kris Jenner has taught her well!

Skimpy swimwear isn’t the only trend Kylie’s showing off. Cosmopolitan revealed that Kylie is already ahead of two of spring 2021’s hottest trends: “psychedelic prints and strappy tops.” Whatever designer duds she wears next, no doubt her millions of fans will take notice. And while it’s clear Kylie has transformed since her tween days, we have the feeling she’s only going to continue to evolve from here.

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