AS Kendall Jenner approaches her 30th birthday, showbiz insider Jordan Paramor charts her journey from shy, insecure teen to potentially the most famous Kardashian-Jenner of them all.
Kendall was never supposed to be a Kardashian-Jenner success story. Along with her younger sister Kylie, she was goofier, less polished and far more awkward than her superstar older half-sisters Kourtney, Kim and Khloé.
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We take a look at Kendall Jenner’s rise from shy teen to global superstar as she nears her 30th birthdayCredit: WWD via Getty Images
Kendall with sister Kylie and parents Kris and BruceCredit: WireImage
Kendall with Caitlyn, who she still calls dadCredit: Getty Images
So, how did the shyest member of Hollywood’s most famous clan rise to become one of the most in-demand models in the world?
From Chanel to Balmain, she has walked the runway for every major fashion house, appeared on numerous Vogue covers and, in 2017, was named the world’s highest-paid model.
As she prepares to turn 30 on November 3, Kendall’s star has never been higher, with rumours that she’s even in the running, alongside the likes of Sydney Sweeney and Sabrina Carpenter, for the latest Bond Girl role.
Now, an insider close to the family reveals that Kendall will celebrate her milestone birthday in style – whether she likes it or not.
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“She may not be the most outgoing of the siblings, but Kendall is very close to her family, and they won’t let her 30th pass quietly.
“She’ll be having a party one way or another. Her mum, Kris, turns 70 two days later on November 5, so they may have a huge joint bash and the attention won’t be all on Kendall.
“There’s also talk of a trip away with her closest friends. Vegas has been mentioned, but the birthday girl thinks it’s a bit flashy for her.
“She would rather do something more low-key. She loves skiing and enjoys the fun of the après-ski, so that’s a possibility. Whatever Kendall does, it will have a cooler edge to it.”
‘I was born into this life, but I didn’t choose this life’
She was just 11 when she was catapulted to superstardom via TV series Keeping Up With The Kardashians. While her sisters always appeared to embrace the limelight, Kendall has never been quite as comfortable, admitting in 2023: “Since I was really young, I felt out of place in my family. I was born into this life, but I didn’t choose this life.”
As a result, her relationships with her sisters haven’t always been smooth sailing. “She loves her sisters and would do anything for them,” says the insider.
“But she isn’t a fan of all the drama and often makes that clear. It’s important to her that she stays away from scandal so she can keep up her sophisticated image.
“She is closest to Kylie [28], and even though they used to clash a lot, things have calmed down as they’ve got older.
“She knows she can always turn to Kim [45], Khloé [41] and Kourtney [46] whenever she needs help or advice, and Kim in particular is someone she can confide in – she’s been through more than the rest of the siblings put together, and always takes care of Kendall.”
Few could have predicted Kendall’s meteoric rise to the top of the notoriously high-brow fashion world, especially considering her reality TV beginnings.
In fact, the first mention of Kendall’s modelling career emerged as a plotline in KUWTK in 2009, when showbiz’s most famous “momager” Kris Jenner (the term was even coined for her) took the then 14 year old to a meeting at esteemed agency Wilhelmina Models.
Kendall cannot act like this diva who’s really difficult to work with. No one’s going to want to work with her
Sister Kim
She was signed on the spot, although the scenes gave major stage-mum vibes – it seemed as if Kris was keener for her daughter to become the next Christy Turlington than Kendall was.
The following year, in season six of KUWTK, things didn’t bode particularly well either, after Kim hired a coach to help her younger sister hone her awkward runway walk. A sulky, bored 15-year-old Kendall was having none of it.
“Kendall cannot act like this diva who’s really difficult to work with,” Kim ranted. “No one’s going to want to work with her.”
Although it took her a while to perfect the ultimate strut, at 5ft 11in and naturally lean, Kendall was a designer’s dream.
As well as being willowy and striking, she garnered plenty of coverage, effectively providing free publicity for every brand she modelled for.
By the time she was 18, she had landed covers for Seventeen and Teen Vogue, along with campaigns for Forever 21 and high-end dress designer Sherri Hill.
She was establishing herself as a force to be reckoned with. Now, all she had to do was get people to take her seriously.
Fed up of others assuming her success was due to her famous family, she even decided to drop her surname from her modelling portfolio.
A publicity shot from The KarsadiansCredit: Unknown
Posing with sisters Kim and Kylie back in 2010Credit: WireImage
Kendall has not been immune to scandal, as the ‘tone deaf’ Pepsi ad showedCredit: Pepsi/XPOSUREPHOTOS.COM
With sister Kylie in 2008Credit: Getty Images
“What I have has almost worked against me,” she said. “I had to work even harder to get where I wanted. People didn’t take me seriously as a model, because of the TV show.”
‘As a model, why would I have my face reconstructed? It doesn’t even make sense’
For all her hard work, however, Kendall hasn’t been immune to scandal. In 2017, her career took a serious misstep when she appeared in a controversial ad campaign that showed her averting a potential clash between protestors and police by giving an officer a can of Pepsi.
The ad was labelled “tone deaf”, and accusations of white privilege came thick and fast, before Pepsi pulled the promo.
“I just felt so f**king stupid,” Kendall later said of the controversy on an episode of KUWTK.
“The fact that I would offend other people or hurt other people was definitely never the intent. I genuinely feel like sh*t and I have no idea how I’m going to bounce back from it.”
My dad is my dad, but he’s not there physically any more. But she lets me call her ‘Dad’. That’s the last little piece of Dad I’ve got
Kendall on Caitlyn
Away from the catwalk and the cameras, she had plenty to contend with behind the scenes, too, not least the divorce of her parents in 2015.
Her father, former Olympian Bruce Jenner, came out as a transgender woman, Caitlyn, soon after.
Kendall said of her dad’s transition: “I’ve known since I was a kid. He never confirmed it to me, but I’ve known for a very long time.
“It’s the same person. My dad says it herself sometimes, it’s kind of like mourning the loss of someone, because it is.
“My dad is my dad, but he’s not there physically any more. But she lets me call her ‘Dad’. That’s the last little piece of Dad I’ve got.”
The 29 year old has also faced endless speculation about what plastic surgery she’s had to achieve her flawless face.
It’s something she has always denied, despite being pictured leaving a building where surgeon to the stars, Dr Jason Diamond, has an office, wearing a white full-face collagen mask.
Talking to fans during an Instagram Live in 2017, she candidly addressed the rumours.
“All of a sudden, photos of us came out with headlines like: ‘OMG Kendall got her lips done and got full facial reconstruction – look at her cheekbones, look at her nose!’ I was like: ‘This is crazy,’” she said.
“As a model, why would I have my face reconstructed? It doesn’t even make sense.”
She has been equally candid about the skin problems that have plagued her for years, sharing on Instagram in 2019: “While there are much bigger problems happening in the world, suffering from acne for me was debilitating.
“It’s something that I’ve dealt with since I was a young teen and has caused me to feel anxious, helpless and insecure.”
It’s a vulnerability she revealed again during an interview with Vogue last year, in which she said she has suffered with anxiety since she was just seven years old, and admitted to recent problems with her mental health.
“I’m a negative thinker. That’s my problem. I’m always worrying about something that may never happen. I don’t see why I shouldn’t be honest about it,” she said.
“In my career right now, I feel really stable, really hopeful. But I’ve had a tough two months. . . I’m more sad than usual. I’m way more anxious than usual. So I’m not going to sit here and act like everything’s perfect.”
‘I personally think that bringing relationships into the public makes everything so much messier’
Thankfully, as well as her tight-knit family, she has plenty of close friends to lean on when things get tough.
With one of the coolest squads in showbiz, her inner circle includes fellow supermodel sisters Gigi and Bella Hadid, as well as Hailey Bieber, Cara Delevingne, Alessandra Ambrosio, influencer Fai Khadra, Willow and Jaden Smith, and singer Miley Cyrus.
“She is especially close to Gigi and Bella. They’ve been friends since their teens and started modelling around the same time,” reveals a source.
“You would expect there to be some rivalry between them, but they’re genuinely happy to see each other do well.
“They all understand the business well, so they support each other through the ups and downs.
“It’s incredibly important for Kendall and her family to be able to trust the people around them implicitly.
“Kendall has always been particularly careful and, as a result, she has been able to keep her private life private and largely control her image in a way that she wants.
Paris Fashion Week this year, with Cara Delevingne, Cindy Bruna and Eva LongoriaCredit: JM HAEDRICH/SIPA/Shutterstock
Kendall with bestie Hailey BieberCredit: WireImage
Taking a blonde look for L’OrealCredit: Getty Images
Early modelling job for Sherri HillCredit: WireImage
“She never wants people to think badly of her, and her friends have always got her back. It’s not an easy circle to infiltrate.”
She has made a concerted effort to keep her private life out of the public eye. So far, none of her boyfriends have made an appearance on either KUWTK or The Kardashians, the Hulu reality show that has run since 2022.
“I got a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that,” she explained.
“For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier.”
Like everyone, Kendall’s life isn’t without its problems, but she is rich, beautiful, has a wonderful family, amazing friends, and she’s turning into a savvy businesswoman
There were rumours of a romance with Harry Styles following his split from Taylor Swift in 2013, and in January 2014 the pair were pictured with friends on a ski trip in Mammoth Lakes, California.
They were linked again two years later when they spent New Year’s Eve partying on a private yacht in St Barts.
Neither have ever confirmed they were a couple, but when her sister Khloé was asked directly about the romance, she replied: “They were hanging out together. Do I think they’re dating? Yes.”
Kendall has also been linked to rappers Drake, Bad Bunny and A$AP Rocky, who now shares three children with pop icon Rihanna.
It appears Kendall also has an eye for basketball players, with Jordan Clarkson, Blake Griffin, Ben Simmons and Devin Booker all rumoured to be on her dating roster.
In contrast to her usual under-the-radar relationships, she and Devin went Instagram official on Valentine’s Day 2021, before splitting up in late 2022.
After three years apart, the duo are thought to have rekindled things earlier this year, and were seen leaving the same hotel to attend a New York Fashion Week Vogue party in September.
While Kendall apparently still refuses to call the Phoenix Suns player her boyfriend due to “trust issues”, sources say their on-off union is currently very much in play, with one telling American entertainment magazine US Weekly: “Kendall thinks Devin is really funny, and they seem very solid right now.”
With campaigns for Calvin Klein, L’Oréal Paris, Chloé, Balmain and Fendi to her name, a seemingly steady relationship, a blossoming acting career, her drinks brand 818 flourishing and recently announced as Therabody’s new global ambassador, Kendall has plenty to be grateful for as she turns 30.
“Like everyone, Kendall’s life isn’t without its problems,” says our insider. “But she is rich, beautiful, has a wonderful family, amazing friends, and she’s turning into a savvy businesswoman.
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“She’s at the top of the modelling game and she has big plans for the future.”
Imagine what she’s going to achieve by the time she’s 40. . .
Out with fellow model and friend Bella HadidCredit: Getty Images for Vogue
Kendall with on-off boyfriend basketball stat Devin BookerCredit: Getty Images
Kendall has also been linked to rappers Drake, Bad Bunny, above, and A$AP Rocky, who now shares three children with pop icon RihannaCredit: Getty Images
Having fun with KylieCredit: Unknown
