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E! Online (US) - Top Stories

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Kylie Jenner Shares If Kris Jenner and Caitlyn Jenner Wer...
Marissa Dow · 2026-05-15 · via E! Online (US) - Top Stories

Kylie Jenner Shares She Was on Bed Rest During Pregnancy With Son Aire

Kylie Jenner may be king, but the title that changed her the most is "mom."

When the Kardashians star got pregnant with her daughter Stormi Webster at age 19, she admitted she was nervous to tell parents Kris Jenner and Caitlyn Jenner. Though Kylie had already made up her mind about motherhood, it was a huge moment to see how they'd redact to her news. 

"I was freaking out. I was really scared to tell my parents,” the 28-year-old said on the May 14 episode of Therapuss. "But there was something just inside of me that I wanted to do this.” 

"And then I told my mom," Kylie continued between happy tears. "No one was angry at me. It was crazy times."

Indeed, Kylie appreciated the support from her loved ones, though she knew becoming a mom was a challenge only she could decide to take on. "I had to make a decision for myself. What do I really want, what can I handle?" Kylie asked herself at the time. "Even if I have to do this alone or however, this is the choice I'm gonna make."

Looking back at the big decision reminded the Kylie Cosmetics founder how far she's come with Stormi, who she welcomed with ex Travis Scott in 2018, before they had their son Aire Webster in 2022. 

"I've entered a different stage of motherhood," Kylie said. "I'm in 'I have an 8-year-old' stage. She's my age when we started Keeping Up With the Kardashians, almost."

Since starring in KUWTK—which premiered in 2007—Kylie has turned her career into a billion-dollar empire. So what does Stormi know about the legacy she started with her aunts Kourtney Kardashian, 47, Kim Kardashian, 45, Khloe Kardashian, 41, and Kendall Jenner, 30?

(Photo by Phillip Faraone/Getty Images for Kylie Cosmetics)

"She knows Mommy makes makeup," Kylie—who is now dating Timothée Chalamet—shared. "She loves to go to Ulta, shop for makeup and other products. She likes to buy my things, and she likes my lip butter."

Stormi is also aware that the reality star is "always leaving for work" because of her many businesses. "I’m super involved," as Kylie recently told Vogue of her clothing brand Khy in an interview published on April 27. "I’ll start with an inspiration board, then it moves from inspiration to sketches. Then, I like to see a million samples."

For a look at Kylie's biggest wins over the years, keep scrolling...

Rick Kern/Getty Images for Ulta Beauty

Kylie's Empire

Kylie Jenner started out the decade as a teenager and is ending it as arguably the most financially successful sister in an already successful family.

The star launched Kylie Cosmetics in 2015 and, just a few years later, the company's valuation clocks in at over a billion dollars. In fact, the makeup mogul just sold a majority stake in her cosmetics line for a whopping $600 million.

That kind of cash flow gave Kylie the title earlier this year as the world's youngest self-made billionaire, an accomplishment she got recognized for on the cover of Forbes magazine.

As if that wasn't already impressive enough, the reality star also had her own show on E! this decade, with Life of Kylie premiering in 2017 for a season that peeked inside the celebrity's personal and business life.

E!

Kylie's Viral Moments

Kylie has brought us some of the past decade's most memorable viral moments that keep on giving.

In 2016, Kris Jenner gifted Kylie a baby pig...or should we say chicken? At least, that's what Kylie thought when she famously squealed, "Is that a chicken?" The moment instantly went down in pop culture history and we're still sending GIFs to this day of her misidentification of the little piglet.

Earlier this year, Kylie also had the Internet abuzz when she gave a tour of her Kylie Cosmetics office, including a peek inside Stormi Webster's nursery. When she hit on the lights, she sang out, "Riiise and shine," and the moment immediately went viral with fans creating tribute videos recreating the moment.

Getty Images; Instagram; Pap Nation/SplashNews.com

Kylie's Style

Kylie proved over and over this decade that she is a style star with some of the decade's hottest looks.

Who could forget when she and sister Kendall Jenner hit the pink carpet together at the Met Gala? The duo fully embraced 2019's camp theme, with Kylie serving looks in a custom-made lavendar Versace dress adorned with feathers.

She also was best dressed (other than the bride, of course!) at Hailey Bieber's wedding in a metallic gold dress that turned heads. The reality star also channeled her inner Barbie last year in a silky pink dress to celebrate her 21st birthday.

We can't wait to see what looks Kylie will rock in 2020, too!

Dia Dipasupil/Getty Images

Kylie's Relationships

The star had a decade full of romance, with rumored flings like Cody Simpson and Jaden Smith kicking off the decade.

Later in the decade, the two biggest beaus we saw the celebrity date included Tyga, who dated Kylie on-again, off-again for two years.

Then, in 2017, Kylie started dating Travis Scott. Though the two decided to take some time apart just a few months ago, they continue to raise their daughter, Stormi Webster, together. They even coordinated surprising the 1-year-old this Christmas with a visit from Poppy, her favorite Trolls movie character!

E!

Drama

While the decade was full of highs for Kylie, there were also some lows, most notably the very public fallout with her former best friend, Jordyn Woods.

Earlier this year, there was a media frenzy around Woods allegedly kissing Tristan Thompson, Khloe Kardashian's then-boyfriend, at a party. And while most of the focus was on Khloe and Thompson, who ended up splitting, Kylie's friendship with Woods was also thrown into chaos.

On Keeping Up with the Kardashians, we saw Kylie struggle with both how her family was acting towards Woods in public and her own decisions on if the friendship was over. Ultimately, after plenty of tears, the reality star called it quits, leaving that friendship in this decade.

Instagram

Kylie's Family

One of the biggest highlights of Kylie's decade had to be the birth of her first child, Stormi.

Kylie shocked everyone when, in early 2018, she welcomed her daughter into the world after successfully dodging the press. On Keeping Up with the Kardashians, sister Kim Kardashian even joked that Kylie's pregnancy was, "The best kept secret of our generation."

Now, the new mommy loves to spend time with her daughter as much as she can, from getting her a two-story playhouse this Christmas or getting some quality time in at her Kylie Cosmetics office, where she has a nursery for her little one.

AKM-GSI/Backgrid; Instagram; Getty Images

Kylie's Transformation

Kylie had plenty of transformations this decade, such as going from a teenager to an adult, but a few of her fashion and beauty transformations were truly unforgettable.

For example, we remember when Kylie was suddenly rocking blue, then green, then super blonde hair, and couldn't figure out how she was switching up styles so frequently until the star showed off her wig collection on the (now defunct) Kylie app. Her dramatic hairstyle colors inspired us to hit the salon to change up our tresses, too.

Kylie also famously got her lips filled, which she credited to feeling insecure about them, giving her a new, signature pout that made her lip kits all the more desirable when they launched.

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