Random romances, playing favorites, and teen girlbossing.
Turns out there's more to this nepo baby billionaire than we thought.
As a member of the Kardashian-Jenner clan, Kylie Jenner has been in the spotlight since birth.
In fact, the future makeup mogul was just ten years old when "Keeping Up with the Kardashians"
first hit E! in October 2007, making her an extremely young reality TV star.
As a result, Jenner knows what it's like to grow up as a celebrity, experiencing all of
the good and bad that goes with that.
She told Vanity Fair Italia,
"Notoriety, exposure never got in the way of my personality.
Fame came early in my life, in a way I can say it came naturally because I can't define
a real before or after — it has always been that way."
Despite finding her own sense of ease with the humongous level of fame she's experienced
since she was a child, Jenner has also been forced to deal with the negative side of fame,
which has continued to affect her as an adult.
In 2015, she told Interview,
"I wake up every morning with the worst anxiety.
[...] I wake up every morning at, like, seven or eight because I think that there's a bad
story about me, and I have to check.
My worst fear is waking up and finding something bad about me on the internet."
It's clear that the intense experience of being famous has undoubtedly changed Jenner's life.
Throughout her life, Jenner has always remained close with her parents, Kris and Caitlyn Jenner.
In fact, in September 2022, Kris got into hot water during an appearance on "The Late
Late Show with James Corden" when she was hooked up to a lie detector test.
Kylie asked her mom a potentially controversial question.
"Am I your favorite child?"
"Yes."
The lie detector confirmed that Kris was, indeed, telling the truth, to which the iconic
momager joked she couldn't go home, in reference to all of her other children finding out about
her answer.
Whether or not Kris really has a favorite child remains unclear, but if the lie detector
test results are any indication, she seemingly holds Kylie in high esteem.
In February 2023, Kylie also celebrated Caitlyn's influence in her life, telling Vanity Fair Italia,
"My father has always been there.
At school, at all the plays, at sporting events.
She was always there.
She taught me one of the most important lessons: to learn to respect yourself, not to be afraid
of who you are.
It is a fundamental lesson."
While Caitlyn and Kris introduced Kylie to the world of celebrity from a very young age,
it sounds as though they've supported their daughter every step of the way, both on and
off screen.
Jenner seems like she has her life pretty together now, but apparently, her teenage
years were a little more messy.
When asked if she ever rebelled as a teenager, Jenner told Homme Girls,
"I stole my mom's car a lot.
Because we grew up in Calabasas, which is outside of the city, it was very crazy if
you went like 45 minutes into LA.
It was a whole new world.
So, I used to steal her car."
While it's unclear how Kris Jenner felt about her youngest daughter taking her car without
her permission, it's most definitely a surprising revelation from the Kylie Cosmetics founder.
"Dad, you are so annoying and I'm never gonna talk to you again because you always do this –"
While Kylie wasn't always on her best behavior as a teen, she's also revealed that it was
sometimes challenging growing up as a reality TV star.
Speaking to Interview, Kylie revealed,
"I feel like I'm going to look back and be like, 'Damn, I wish I could've just been a
kid and done normal teenage stuff that my friends get to do.'
But it also is a blessing, and I've done so many things that most 35-year-old women still
haven't done."
Jenner's life changed immeasurably when she founded her makeup company, Kylie Cosmetics.
In fact, when the reality star launched her very first lip kit in November 2015, the product
instantly sold out, proving that she'd created something fans really wanted.
In 2019, it was announced that Jenner had sold a 51% stake in her cosmetics company
to global brand Coty, which netted her a whopping $600 million.
While Jenner has been involved in many business ventures, it's clear that Kylie Cosmetics
remains the most important.
She told Homme Girls,
"I think my love in life, my passion, is makeup.
That's where it all started.
It's what keeps me going every day, being creative on Kylie Cosmetics."
Luckily, Kris Jenner realized just how serious her daughter was about getting into the makeup
business, and it wasn't long before Kylie found major success.
"It's kinda weird, I just don't want to talk about my lips.
It's just an insecurity of mine.
It makes me feel a little uncomfortable."
Like most celebrities, Jenner has faced her fair share of accusations regarding plastic surgery.
But according to her, she hasn't had as much work done as some people might think.
She told Homme Girls,
"I think a big misconception about me is that I've had so much surgery on my face and that
I was some insecure person, and I really wasn't!
[...] I had my one lip insecurity thing, so I got lip filler, and it was the best thing
I've ever done.
I don't regret it."
While Jenner's admission that she's had fillers should be enough to appease the skeptics,
the Kylie Cosmetics founder has had to address the claims on multiple occasions.
In 2015, Jenner got candid with Grazia, saying,
"I haven't had plastic surgery.
I've never been under the knife.
People flashback to pictures of me when I was 12 and say 'Kylie's so different' but
how can I look the same from 12 -18?"
While we may never know the truth about what cosmetic procedures the Kardashian family
has had done, it seems that Jenner is comfortable with her appearance, and has admittedly made
some minor tweaks to bolster her confidence as a young woman.
In March 2019, Forbes declared that Jenner had become the world's youngest "self-made"
billionaire on account of her success with Kylie Cosmetics.
In fact, the publication estimated that Jenner's cosmetics brand was worth a whopping $900
million alone.
Of the accolade, Jenner told Forbes,
"I didn't expect anything.
I did not foresee the future.
But [the recognition] feels really good.
That's a nice pat on the back."
However, the celebration was short-lived.
Forbes retracted its proclamation that Jenner was the world's youngest self-made billionaire
in March 2020, claiming that they'd been misled regarding the actual profitability of Kylie Cosmetics.
The discrepancies allegedly came to light after Jenner sold a 51% stake in her makeup
brand to Coty, with paperwork from the deal suggesting that Kylie Cosmetics was a lot
less profitable than it was originally thought.
Still, it's not all bad news for Jenner, as Forbes still estimated that the reality TV
icon was worth a stunning $900 million.
Sure, it's not the cool billion that was initially reported, but it's really not that far off.
Regardless of where Jenner's wealth actually sits, it's clear that her business ventures
have been incredibly successful — with the help of the Kardashian-Jenner empire, of course!
"How are you?
How's the baby?"
"It's been really hard for me."
"How so?
Anxiety or sadness?"
"Well, I cried nonstop all day for the first three weeks."
Jenner's life may seem pretty perfect from the outside, but the makeup mogul has experienced
difficulties just like everyone else.
On February 1, 2018, Jenner gave birth to her first baby, daughter Stormi, having managed
to keep her entire pregnancy a secret.
Her second child, a son named Aire, was born four years later on February 2, 2022.
During her February 2023 interview with Vanity Fair Italia, Jenner opened up about both of
her pregnancies, and her experience with postpartum depression, saying,
"The first time was very difficult, the second was more manageable."
Jenner also offered advice to other people experiencing postpartum depression after giving birth.
She told Vanity Fair Italia,
"I know, in those moments you think that it will never pass, that your body will never
be the same as before, that you will never be the same.
That's not true: the hormones, the emotions at that stage are much, much more powerful
and bigger than you.
My advice is to live through that transition, without fear of the aftermath."
Jenner's candor is an important reminder that reality stars are human beings who face many
of the same physical and mental health issues as their viewers.
By sharing her own experiences of postpartum depression, Jenner has hopefully helped others
feel less alone, and let them know that there is a way through the condition.
As one of the most famous people in the world, and especially as a member of such a polarizing
family, Jenner is no stranger to bullying.
Luckily, the star has been able to gain perspective on the criticism she faces on a regular basis,
and she's offered her support to help others who may be facing similar difficulties.
While speaking to Interview, Jenner revealed why she'd gotten behind the #IAmMoreThan anti-bullying
Instagram campaign.
She told the publication,
"I feel like if I came out and just told my story about bullying, people wouldn't have
sympathy — and I’m totally okay with that, because people don’t need to understand.
[...] But I wanted to give other people who have been bullied, and who overcame it to
do something amazing, the opportunity to use my platform to bring awareness, to inspire people."
During the same interview, the fashion icon went on to explain that she had faced various
forms of bullying since she was just nine years old, which is pretty horrifying to think about.
She said,
"Like, every single day I see something negative about me.
And it's just completely torn me apart.
I feel like I've lost so many amazing traits because I've listened to stupid people, ignorant
people who are bullies."
Growing up in the spotlight obviously had its positives and negatives, but Jenner's
decision to stand up for the victims of bullying shows that she can use her platform to help others.
E!'s "Keeping Up with the Kardashians" and Hulu's "The Kardashians" have tracked the
evolving relationships between the family's famous sisters — Kim, Kourtney, and Khloé
Kardashian, and Kendall and Kylie Jenner.
While Kendall and Kylie are closest in age, Kylie made a huge revelation during an interview
with Vanity Fair Italia in 2023.
When asked who her favorite sister was, Kylie controversially revealed,
"It changes over time.
Right now it's Kim.
Kim has changed so much recently.
We are very connected, she is always the first sister I call when I need something.
We have been going through a lot of similar experiences lately."
"Your lips look amazing."
"Really?
Kendall said they were too big yesterday."
"Are you talking about her lips?"
Conversely, Kylie delved into which sibling she feels the most distant from, telling Vanity
Fair Italia,
"Without a doubt Kendall.
You know what they say, though?
Opposites attract.
And that's how it works with us."
As the youngest siblings in the clan, Kendall and Kylie had a very different upbringing
from their older sisters, and both became reality stars at an extremely young age.
For whatever reason, Kendall and Kylie might not be as close with one another as they are
to their other sisters.
But judging by Kylie's Vanity Fair Italia interview, the connections between the Kardashian-Jenner
siblings are pretty fluid, so Kim might not always be her favorite.
Throughout her life, Jenner has dealt with external bullying and internal insecurities,
all of which must have had an impact on her self-confidence.
Luckily, becoming a mother to two young children helped to build Jenner's confidence back up.
During an interview with British Vogue in April 2023, Jenner revealed,
"Since I've become a mother, being with my kids really makes me feel confident and beautiful.
They love me for me, no matter what."
Clearly, Jenner has built a strong family unit with her daughter Stormi and son Aire,
and her identity as a mother has only added to her own self-worth.
Jenner has regularly made it clear that starting a family of her own was a crucial turning
point in her life.
Speaking to Vanity Fair Italia, Jenner discussed what it was like becoming a mom, saying,
"It's such a unique and special situation and it's all about building with these little
beings that you're learning about.
There is another magical moment, though: when you bring your children home.
It is perhaps the most beautiful moment."
Clearly, the Kylie Cosmetics founder's life has been changed for the better by her children,
and it's given her a focus away from the pressures caused by the world of celebrity she's a part of.
Stormi Webster has been in the public eye since her birth, but that doesn't mean that
Jenner wants her daughter to experience all of the trappings of celebrity just yet.
In fact, Jenner is actually a little worried about Stormi being exposed to all of the online
chatter and potential hatred that she herself experienced from the general public at a young age.
Speaking to Harper's Bazaar in 2020, Jenner revealed,
"Exposing her to all of the negativity that comes with the internet, I think about that too.
I'm just trying my best, even though she's still little, to remind her how blessed we
are and that this isn't normal, the way we live.
It's just our life.
People want to take pictures."
In other words, Jenner wants to protect her children from the spotlight for as long as possible.
Despite attempting to keep her daughter away from the dangerous side of the internet, Jenner
is also hoping that Stormi will play a big part in her company one day.
During an interview with Tmrw, Jenner revealed,
"Stormi is my legacy...
I'm raising her to be smart and kind and driven.
Maybe she will take over Kylie Cosmetics one day."
Whether or not Stormi will have her mother's passion for makeup remains unknown, but Jenner
is definitely doing her best to prepare her daughter for fame.
Jenner hit a career snag in 2017 when her application to trademark the name Kylie was
successfully blocked by Australian pop superstar Kylie Minogue.
As reported by World Intellectual Property Review, Minogue suggested that Jenner trademarking
the name Kylie would confuse the singer's long-term fans, and brutally referred to her
opponent as a "secondary reality television star."
Ultimately, Minogue succeeded in stopping Jenner's application.
During an appearance on "Watch What Happens Live with Andy Cohen" in June 2022, Minogue
discussed the trademark dispute.
"It was just business, obviously."
She further explained that filing her notice of opposition to Jenner's trademark wasn't personal.
"I've spent a lifetime protecting my brand and building my brand, so it was just something
that had to be done [...] We came to an agreement."
It would seem that Minogue has zero ill will towards Jenner, and simply wanted to protect
the name she's been performing under since the late 1980s.
While it's unclear how Jenner felt about losing out on the trademark, her career doesn't seem
to have suffered in the slightest.
Blac Chyna began a relationship with Jenner's brother Rob Kardashian in early 2016, with
the pair announcing their engagement in April 2016.
The following month, it was revealed that Chyna was pregnant with the couple's first
child together, and they welcomed their daughter Dream Kardashian in November 2016.
However, by the end of the year, there was trouble in paradise, and reports of multiple
altercations started to surface.
The couple split for good in February 2017.
After Rob posted nude photos of Chyna on social media, she was granted a temporary restraining
order against her ex in July 2017.
Jenner and her brother subsequently sued Chyna for alleged physical violence against Rob
and for damaging property.
Chyna also decided to sue her ex for defamation and loss of earnings in a $108 million lawsuit,
claiming that the Kardashian family intentionally got her reality TV show "Rob & Chyna" canceled
after just one season.
In April 2022, Jenner took the stand to discuss her brother's violent altercation with Chyna, saying,
"He used the words, 'She was trying to kill me' I assumed that was a death struggle."
Jenner also recalled a message she'd received from Chyna, revealing in court,
"She sent me a bunch of devil emojis and said, 'counting down the days' to beat me."
It seems that there's no love lost between Jenner and Chyna.
Jenner was first linked to Oscar nominee Timothée Chalamet in April 2023.
Early reports suggested that Kylie's sister Kendall Jenner may have helped to introduce
the pair, and that Kylie was on a break from her on-again/off-again partner Travis Scott
when she first started dating Chalamet.
It was later speculated that Scott wasn't particularly happy about his ex dating again,
but that they were continuing to co-parent their two kids, Stormi and Aire.
While some onlookers may wonder what Chalamet and Jenner have in common, it's been noted
that they're both heavily into fashion.
At the Met Gala in May 2023, Jenner wore an outfit designed by Haider Ackermann for Jean
Paul Gaultier.
The very same designer worked with Chalamet to create a bespoke jumpsuit for his appearance
at the Venice Film Festival in September 2022, suggesting that the actor may have connected
with Jenner in a fashion setting.
Whether or not Jenner and Chalamet's romance will become serious is anyone's guess, but
fans of the lip kit guru will be excitedly awaiting the couple's potential red carpet debut.
Once again, Kylie Jenner has defied expectations and surprised us all.