Channelling the golden age of Avedon in the season’s most spectacular couture, Kendall Jenner opens up about fears for her safety, her famous clan, and growing up a tomboy.

Portrait of Tammy Strobel
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Channelling the golden age of Avedon in the season’s most spectacular couture, Kendall Jenner opens up about fears for her safety, her famous clan, and growing up a tomboy.
My Reading Room

“I’m more of a Jenner than a Kardashian”

There are reminders. They come involuntarily, it seems— like hiccups—every few minutes. They pepper the conversation, punctuating nothing of great consequence, but they are useful… necessary, even, at times.

“I’m young,” Kendall Jenner will say when discussing her love life. “But I’m young,” she adds when talking about her first house. “I know. I’m young,” she declares after mentioning how she wants to be a mum some day.

She’s only 21 years old, yet she’s lived a long life. Or at least that’s how it feels. She and her colossally famous parents and siblings have managed to reach into nearly every corner of popular culture like some mutant octopus with an unbreakable choke hold on the collective consciousness.

It feels like they’ve been there—in our heads, on our screens, everywhere—for ages, as much a part of the fabric of the United States as the American flag itself, albeit one that’s been heavily bedazzled and trimmed with fur.

So, yes, the reminders are helpful. Kendall Jenner is, in fact, young. “When I turned 20, I remember being like, ‘Shit! I’m in my twenties.’ Everyone says, ‘These are the best years of your life. Live it up!’” she says. “So maybe I’m just reminding myself.” Who could blame her? Kendall was 11 when Keeping Up with the Kardashians debuted in the fall of 2007, opening her life, and the lives of the rest of the Jenner-Kardashian family, to public examination— and, naturally, criticism. But life moves fast when it’s measured by Nielsen ratings, social media followers and millions of dollars in revenue.

Not that she regrets saying, “Okay,” the day her mother asked her and her little sister, Kylie, if they wanted to be in the television show that was about to start shooting in their Calabasas, California, home.

“We were normal kids,” Kendall says of Kylie and herself.

“The cameras barely even fazed us.” Normal is relative, of course, but to hear Kendall tell it, she had a wonderful childhood. There were horses, dirt bikes and Barbies. There were movie premieres with a superstar dad and hours in front of the TV watching That’s So Raven and The Suite Life of Zack & Cody. And there were her beloved camo shorts, which she took off only long enough to wash—at her mother’s insistence— every once in a while. “She wore those shorts every day,” recalls her mom, Kris Jenner. “She wasn’t the little frilly girly-girl.” She was actually the exact opposite. “I was a huge tomboy,” she says. “I had a phase where I wore boys’ clothes. I was always hanging out with guys. I’ve always connected with guys more.” That’s no easy feat, particularly when Kourtney, Kim and Khloé Kardashian are your big sisters. They’ve taken being girly-girls to stratospheric levels. “I’ve always been the different one,” says Kendall.

“I mean, I’m a girl and I like being a girl, but I’ve just never been into it like they have. I think I get that from my dad. I’d say I’m more of a Jenner than a Kardashian.”

She still doesn’t like dressing up as much as her sisters do, though given her profession, she doesn’t have much of a choice. She documents her life as one of the world’s top models for her millions of Instagram followers and on her blog, which costs US$2.99 a month for access to light fare such as “The Groceries I Always Grab (& Where I Get Them),” “4 Things I Want to Steal From Kim,” and “How Much Are You Like Me?” (That last one is a quiz, which I, a middle-aged father of three with a minivan, got caught looking at, but not taking, on the train to my small suburban town.)

New York Fashion Week has just come to a close, and Kendall is decidedly casual—her hair in a tousled bun on top of her head, what she calls “just a little bit” of makeup, and wearing a Supreme T-shirt, leather pants and a Balenciaga denim trucker jacket— when she arrives for breakfast at a quiet café downtown on Bond Street. Sometimes models are unusual-looking—more striking than classically beautiful. Jenner’s beauty is unmistakable. It doesn’t slowly come into focus as you get to know her. No, it’s right there the moment you meet her. She is gracious and polite, and makes it a point to ask questions, not just answer them. She’s mindful about not name-dropping, referencing “a friend” instead of “Gigi.” Finally, and this is big, she shows up on time. She carries herself like a girl grateful to be living her dream—a dream she’s had for as long as she can remember.

A few days before Labour Day in 2010, Kendall climbed onto a bus for the winding, two-hour trip from Los Angeles to Santa Barbara with the rest of Sierra Canyon School’s incoming ninthgrade class. Shortly after they arrived at a nature lodge on the California coast for their freshman retreat, the teachers started taking the kids through a series of get-to-know-you exercises that were no doubt met with groans from the privileged teens. Kendall, 14 and still a year from her first runway but already a reality-show veteran, was bored. The students were asked to write letters to their future selves. Cue eye roll. Kendall found a shady patch of grass, sat with her back against a tree, and wrote her letter (available for all to see for that low, low price of $2.99 a month), complete with smiley faces, hearts and an undue number of exclamation points.

“Dear me,” she begins, before mentioning that she’s shooting season five of KUWTK. “My goal in life is to become a big time model and travel to really amazing places.”

There’s no disputing that Kendall has done just that. She’s just returned from India and Bangkok, and is flying off to London in a few hours. “She’s not afraid of hard work,” says her father, Caitlyn Jenner, the former Olympic champion known as Bruce Jenner before officially changing his name and gender in 2015. “I told her right from the beginning, the way you’re going to be successful in this life is to work hard. No one is going to hand you anything.” But that’s precisely what people thought was happening when she emerged on the fashion scene a few years ago.

After all, being a Kardashian opens doors. And, let’s face it, while that may not be her last name, it’s impossible to separate her from the well-oiled, camera-ready Kardashian machine. So it was inevitable that some catty catwalkers would whisper. “I think people were afraid to say it to my face,” says Kendall, “but they were probably talking behind my back: ‘She thinks she’s too cool. She’s stuck-up… too into herself.’” Because of that scrutiny, Kendall, now arguably the modelling world’s brightest star, makes it a point to introduce herself to new girls backstage and ensure that they feel comfortable.

She doesn’t like the idea of anyone feeling like an outsider. And when a waitress accidentally spills a drink on the table in front of her, Kendall laughs and quickly helps clean it up. Maybe it’s just the manners she was taught by her “amazing parents,” as she calls them, or perhaps it’s that she doesn’t want anyone to ever think she’s “too cool” again.

Either way, she appears to be something of a regular at the Bond Street café. She knows the menu cold and loves this part of downtown New York. It’s not far from the apartment she usually stays in when she’s in town. This week, however, she was at The Mercer hotel, as the apartment was occupied by its owners, her sister and brother-in-law.

“It’s only a one-bedroom, so I’m not going to sleep in the middle of them,” she says. “Don’t know about cuddling with Kim and Kanye.”
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“I think people always want what they can’t have. It’s nice to have some mystery”

Not that it matters. Kendall hasn’t been sleeping well lately.

Jet lag plays a role, yes. But there’s also been crippling anxiety in recent months. And while Kendall has always been anxious (“my entire life”), this is some next-level stuff . It started to ramp up last August, when she drove to her West Hollywood house and found someone sitting at the edge of her driveway. The man walked up to her car and began banging on the window. Terrified, she was able to drive away and phone for help, but the fear has remained.

(She subsequently testified against him and was granted a five-year restraining order.) Things got even worse in October, when Kim was robbed at gunpoint in her Paris apartment, prompting Kris to beef up security for the entire family.

“There’s a lot of creepy people out there,” says Kris. “We’ve experienced it firsthand. It’s like a fortress now at every house.” (Perhaps, but unfortunately that didn’t stop someone from making off with US$200,000 worth of valuables in a reported burglary of Kendall’s house in March.)

Now Kendall has an armed security guard with her at all times, something she feels safer for having, but has grown to dislike. One accompanies her into the café, buzz-cut and barrel-chested, like a cartoon henchman. “I don’t feel normal,” she says, “and I like to feel as normal as I possibly can.”

And though Kendall’s undoubtedly safer with someone sitting outside her house every night and keeping watch on the other side of the door of every hotel room she stays in, the anxiety has yet to fade. “I wake up in the middle of the night freaking out,” she says.

“Full panic attacks. They wake me up from my sleep, and I need to stand up and I pace and I’m freaking out and crying.”

It’s an unlikely confession from the usually guarded supermodel. There is a self-awareness to Kendall Jenner that manages to swim against the powerful current of her bloodline. She has tried to remain as private as possible for someone with well over 100 million social media followers.

Maintaining privacy can be a tall order when cameras follow you around day and night—both at home with the Keeping Up crew and everywhere outside by the unrelenting paparazzi.

But Kendall works at it. “More than the rest of my family, I guess,” she says of her attempts at privacy. “Just ’cause I think it’s powerful. Plus, I think people always want what they can’t have. It’s nice to have some mystery.”

Yet no amount of personal restraint can stop the rumour mill from churning. Like the time gossips suggested that Kendall had shut down her Instagram account in order to have plastic surgery.

“It’s literally the craziest thing,” she says. “Me and my family will be getting this for the rest of our lives.”

Kendall’s love life has been an area of particular fascination in the media, where her sisters’ relationships have played out with all the grace of a Lifetime movie marathon. There were the rumours that she was dating One Direction’s Harry Styles. Then there was buzz about Nick Jonas. These days it’s A$AP Rocky, at least according to the Internet. None of it seems to faze her.

“I’m not marrying anyone,” she says. “I’m not engaged.

There’s nothing long-term or serious like that in my life. If I’m not fully, fully in it with someone, why would I make it public to everyone else? If I don’t even know what it is, why would I let the world know?”

She’s witnessed first-hand the pressure and strain that publicity can put on a relationship. “I think it’s something sacred,” she adds.

“It’s something between two people, and nobody else’s opinion needs to be involved in it. People want to start drama. If I had a boyfriend, people are going to say all this stuff that’s probably going to cause us to break up.”

Okay, that makes a lot of sense, but is she dating anyone special?

“I’m doing my thing,” she says with a smile. “I’m having fun. I’m being young.” She answers but doesn’t answer with the ease of a seasoned political insider.

“Kendall has the gift of being able to edit out the noise,” says Kris. The noise grew to deafening levels in 2015, when Caitlyn went through a remarkably public gender transition. Despite incredibly strong relationships with her mum and her sisters, Kendall has always been a daddy’s girl. “When she was born I was managing Bruce’s career, so I had to work every day,” Kris recalls. “Bruce was a huge part of driving her around, doing carpool and stuff . [Caitlyn] has always been very close to her.”

They say a daughter’s love for her father is unrivalled, and that is certainly the case with Kendall. But as she grew into a teenager, she started to sense that something was different. She and her sisters would find clues around the house. A wig here. Some nail polish there. “It was like an investigation for a really long time,” says Kendall. “We would find little things and think, ‘This isn’t normal.’ For a minute, we were like, ‘Okay, is he cheating?’ And then we’d say, ‘I don’t think so.’”

“My biggest concern from the beginning was that I not do anything that would hurt my children,” says Caitlyn. “Along the way, when I was sneaking around in the dark, I got caught a couple of times. I thought I was being smart, and in some cases, well, things happened.”

By the time Caitlyn told the kids, Kendall says she already “kind of knew” but had been in denial. “When she told us, and told us that it was going to be a real thing, it was an emotional couple of months,” she says. “And if I would talk about it, I would cry, just because you’re mourning someone… losing someone. The person is still there, of course, but physically you’re losing someone. It was my dad who I grew up with my whole life and who raised me. It’s an adjustment, for sure. But honestly, you start to realise that this person is still alive. This person is still here. They are still a blessing. They are still awesome. I realised I should just be thankful that I still have my dad. It starts to just become normal.” Kendall still relies on her father as much as she ever has, calling on her often for advice, particularly when it comes to collecting cars.

“We have a special bond,” adds Caitlyn, “because she’s a lot like me in so many ways. Hardworking. Athletic. She loves the car stuff . And I couldn’t be more proud of her.”

It’s easy to forget, perhaps, that Kendall’s family—what with all the various fashion lines, beauty products, video games, tabloid covers, debates over public restrooms, divorces and Kanye—is a real family and not just a group of well-paid character actors who scurry back to their own lives after someone yells, “Cut!,” and the glow of the klieg lights fades.

“I don’t think of it as ‘the Kardashians’ in quotes,” says Kendall.

“I think of it as my family. It’s probably hard for anyone else to understand that, but it’s so normal for me.”
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