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The Real Deal

How did Kendall Jenner transcend childhood TV infamy, the paparazzi—even her own famous family—to become the breakout model of her generation? By owning it.


By Jonathan Van Meter
Photos by Mert Alas and Marcus Piggott Fashion editor: Tonne Goodman
10 min

Above Image | KICK OUT THE JAMS: “Kendall’s not giving her power away,” says Cindy Crawford. “She’s already light-years ahead of where I was at her age.” Hood By Air sweatshirt, trousers, and boots.

On a Tuesday morning in June I meet Kendall Jenner in the lobby of her high-rise in Westwood, that weird part of L.A. that seems to want to be part of a different city, like Dallas or Atlanta. The neighborhood is sandwiched between Beverly Hills and Brentwood, and for most of the Angelenos I know, it is just a dreary canyon of ugly condominiums that one must drive through to get to the groovier shores of Venice or Malibu. Kendall, who grew up in the Valley, bought a two-bedroom condo here for $1.4 million with her own money when she turned eighteen, partly as a way to announce her independence from the Kardashians of Calabasas—and her building looks nothing like the monstrosities nearby. Indeed, from a distance it tricks the eye: Deco? Beaux-Arts? When Kendall appears in the lobby—wearing skintight black jeans, a studded black belt, a teeny-tiny spaghetti-strap top that looks like a bathing suit, and white sneakers, with a furry little purse tucked under her arm—I inquire about the building's provenance. Is it old? I ask, still puzzled. “It is!” she says. “It was built in the eighties!”

Kendall Nicole Jenner was born in 1995, one month to the day after the O. J. Simpson verdict was announced (Kendall's mother, Kris, was the best friend of Simpson's murdered wife, Nicole—hence Kendall's middle name—while Kris's ex-husband, Robert Kardashian, famously defended Simpson). The round-the-clock cable-news circus and paparazzi culture that we now wearily take for granted had just begun to change the way we process the events of the world—essentially, in mind-numbing detail. That August, the Internet suddenly appeared in millions of living rooms for the first time when the Web browser Internet Explorer came bundled with Windows 95. Kendall was just two when The Truman Show landed in theaters like a prophecy from the gods: the story of a boy who unwittingly grows up as the star of a reality show, his every move documented by cameras, broadcast live 24 hours a day across the globe. All of which is to say that Kendall grew up utterly and completely a child of the modern digital-reality-celebrity-besotted culture we now live in. For all intents and purposes, she is child zero, born smack dab on the fault line of a tectonic paradigm shift and raised in the belly of this strange new beast, experiencing nearly nothing of the world that came before.

Perhaps that's why she drives a 1957 Corvette Stingray. We head downstairs from her lobby to the parking garage beneath her building, and there she is: a pristine, robin's-egg-blue convertible that reportedly cost a hundred grand. (When Kendall decided on vintage, her father took her to the hangar in Burbank where Jay Leno keeps his car collection so she could window-shop.) We slide into the creamy white leather bucket seats. “The engine has been restored,” she says, “and it's been repainted, but in the original color. Everything is how it was.” How it was in 1957: no seat belts; one rearview mirror the size of a lady's compact; an AM radio; an engine that burns through a tank of gas on a trip to the grocery store. But it sure is pretty—and fun to drive!

She pulls out of the garage and gracefully slips into the blur of traffic on Wilshire, seemingly possessed of 360-degree situational awareness. When I ask when she learned to drive a stick, she says this: “My dad taught me when I was sixteen in her Porsche.” The dissonance is something you eventually get used to around Kendall. Later, she will slip a few times and call her dad “he,” clearly still adjusting to the new reality of Bruce's having become Caitlyn.

We pull up to a red light, and a middle-aged woman next to us in a Range Rover shouts, “What a beeeeuuuuutifuuul caaaaar . . . . ” Kendall bats her eyelashes. “And I love the lady driving it,” says the woman. “I'm telling you, I get hit on by the most random people,” says Kendall. “Old men—like, older-than-my-dad old—honk at me and wave. Guys on motorcycles will pull up next to me and be like, ‘Nice car! It's your dad's, right?’ And I'm like, ‘No, it's actually mine.’” She downshifts and pulls up to another stoplight, then turns and fixes those big brown eyes on me and deadpans her best line of the day: “It's not necessarily the most discreet form of transportation.”

This reminds me of the famous story of Diana Ross driving around Beverly Hills in the eighties in a lurid yellow Rolls-Royce (owned earlier by both Liz Taylor and Marilyn Monroe), recognized everywhere she went. “Amazing!” says Kendall. “There's this woman here—I'm blanking on her name; it will come to me—who drives around town in a hot-pink Corvette.” Angelyne? I say. “There you go! I still see her every once in a while.” Kendall vaguely knows the history. “Someone paid for a bunch of billboards to make her famous or something?” Indeed. Google “famous for being famous” and up pops a Wikipedia entry: “People who have been described as ‘famous for being famous’ include Angelyne, Paris Hilton, Katie Price, and the Kardashian family.”

Ironically, it is Kim Kardashian West who tells me how Kendall—who, in just two years, went from modeling long shot to VOGUE cover girl with an Estée Lauder contract, undeniably now at the apex of her profession—was self-directed about her career from the time she was thirteen. “She had her eyes focused on exactly what she wanted to do,” says Kim, “and she made it happen.” Kendall wanted, in other words, to avoid the fate of her sisters—to be careful about fame for fame's sake, to be known for something solid and tangible. “Obviously, my success came after my sisters'—I got to see all of their mistakes and watch out for them,” Kendall says. In some ways, she is reminiscent of Linda Evangelista, who also knew she wanted to be a model from the time she was a little girl hanging out in her bedroom, practicing her runway walk, cutting up fashion magazines. Both of them essentially willed it to happen, which is rare. Most models are discovered and wind up doing it because, well, why not? It's often the best option they've got. But when the goal is modeling, heartbreak and disappointment usually follow—after all, Fashion decides who gets to be a model and who doesn't. But there is another reason Kendall reminds some of Linda: Like Evangelista in the early nineties, she is now on equal footing with the stylists and the photographers she works with—an active participant in her own photo shoots. She is, in other words, not just a girl for hire but, more often than not, the reason for the pictures in the first place, as in: This is a Kendall story.

We pull up to another stoplight just before an entrance ramp to the 405. “Time to put my hair up,” Kendall says as she pulls a rubber band off her wrist. Just as she is about to accelerate, a pedestrian appears out of nowhere to cross the street. “Excuse me, sir—little blue car coming through!” Kendall yells, and then floors it. Soon we are roaring along at 70 miles an hour through several lanes of traffic lousy with freight haulers and tailgating commuters. I reflexively reach for the seat belt that isn't there when it dawns on me: I am in a death trap. I would feel safer going over Niagara Falls in a wooden barrel. “You've got to be committed when you get in this thing,” Kendall says with a knowing smile. “You have to know what you're getting yourself into.”

As we pull into the parking lot of Sherman Oaks Castle Park—a city-run “entertainment center” with three miniature-golf courses, an arcade, and batting cages—Kendall says, “I love that no one followed us,” by which she means the paparazzi. Since the paps wait outside her building every day, she is puzzled as to why they have chosen this Tuesday to leave her alone. “Is there someone more interesting around? Like, is Beyoncé in town?” She laughs. We decide to play miniature golf, but Kendall is terrible at miniature golf, so we bail and find a picnic table next to a row of vending machines, she gets a package of Dippin' Dots, and we sit down and talk.

Like the person formerly known as Bruce, Kendall is tall and athletic, with an impossibly long torso. She excelled at track and field and soccer in school. Also like her father, she is constitutionally a loner; she spent a lot of time in her room playing video games. “I remember crying in my bedroom about the fact that Kylie had so many friends and I didn't,” she says. And from about the age of six, she spent as many hours as the day would allow at a barn near where she grew up, riding ponies. One particular horse, Ladybug, was a decent jumper. “She knew better how to do what she was doing than I did,” Kendall says. She likes getting dirty, working with her hands, figuring stuff out.

“We had ATVs and go-carts, and I grew up riding them all the time, which is why I'm a good driver,” Kendall says. “It's superironic to think about now, but it's something I can thank my dad for: how much of a tomboy I was. That's why I think the whole thing—her transition—was really hard for me, because I was like, ‘But you taught me everything tomboy!’” It has gotten easier. “I knew it was going to have its rough phase,” she says. “But it's all supernormal now. It's not weird at all. Sometimes I look at a picture of my dad when she was a guy, and it makes me a little sad—I get emotional. You have to get past it—you've got a new person to love. It's kind of a blessing in disguise—if that's not the wrong way to say it,” she says, and then laughs at her choice of words.

Part of what must seem a bit disorienting to Kendall is that her father now has more in common, at least on the surface, with all of the other women in the family. “I've always been superdifferent from all my sisters, especially my Kardashian sisters. They've always been into the glam thing and dressing up every day and being in the thick of it. Part of me loves that, but at the same time, I love dressing down and having my private life. It's almost, like, empowering to know that no one knows we're sitting here right now—because it's not usually like this. Every day, I have to find a way to escape; I have to go borrow someone else's car. Sometimes it takes me an hour to figure out how to get rid of these guys who have been following me all day. And the second that I feel it getting the better of me, I have to go chill myself out—go take a bath or something to, like, disconnect from it. It keeps you real and sane and humble.”

Indeed, Kendall does have a reputation among fashion people for being grounded, always on time, a grown-up. “If I'm being honest, my little sister and I have every right to go crazy,” she says. “You would expect that from us. But neither of us has the desire to do that. I think it says a lot about the way we were raised. Not even just by my parents, but my Kardashian sisters and what they've taught us. My parents did something right, and thank God.

Though it's kind of hard to square the idea of a mother who cast her young children in a reality show—Kendall was eleven when Keeping Up with the Kardashians started airing—as having done something right, the more you get to know this family, the more it makes sense: They are close-knit, hardworking, and tough. But although Kendall Jenner is a surprisingly good conversationalist—veering back and forth between teen jargon and adult pronouncements, game to talk about almost anything—she is not quite yet ready to think anything negative about her mother's decision to put her entire family in front of the cameras to be picked apart and mocked as shallow and acquisitive. When I mention that the name Kardashian now stands for something—that it's an adjective and not always a nice one—her eyes grow wide, like she's hearing this for the first time. “Oh, my God. I toadully get what you're saying,” she says. “People say a lot of what they think, and it's not always positive. And we never say anything. We just take it. And then when people meet us, they're pleasantly surprised. Because we aren't what people think. One of the best lessons I ever learned from my sisters is not to take everything so seriously. Just leave it alone—it will pass in a week. That's how I grew up. My sisters are so fucking strong, and they taught me and my little sister to just toughen up and not let it affect us. You know what's real.”

Reality TV seems to cheapen everything it touches, including the viewers; it has made us more cynical, not less. Which only makes Kendall's success in an industry built on luxury, exclusivity, and a bit of mystery that much more surprising. “I think being a Kardashian worked against her,” says Kim. “Coming from a reality show, people look down on that—a lot of people in the fashion industry don't respect that world.” Even Kendall had serious doubts. “Two years ago, when I first started this, I thought: This is going to be so embarrassing. No one is going to accept me, and it's going to be a complete failure.” Not exactly. But it did take a pop-culture maven like Marc Jacobs to jump-start Kendall's career by casting her in his fall 2014 show (and then in every show and two ad campaigns since), thereby giving the rest of the fashion world permission to think of her as cool. “We wanted to book her on her merit as a model,” says Jacobs, “not because she's a Kardashian. Every bit of her success is a testament to her hard work and her passion.”

It is also a testament to one very wise decision she made early on. “Marc invited my whole family to that first show, and I was like, ‘I love you guys, but can you please just not come?’ I was trying so hard to be taken seriously, like, ‘Guys: This is not a joke or a stunt; this is what I want to do with my life.’ I had to prove that I could do it.” She sighs deeply, the sense of relief that it all worked out as palpable as if it just happened yesterday. “And now I feel like I'm a part of something. I feel I have accomplished something that is mine.”

The first thing I notice when I walk into Kris Jenner's house in Hidden Hills, the horsey gated community in Calabasas where Kendall grew up, is a giant framed black-and-white photograph of Elizabeth Taylor flipping a double bird to the camera.

“Isn't that funny?” says Kris as she greets me at the door. I have come for a home-cooked meal—pasta and chicken and broccoli. The house is enormous, with twin spiral staircases descending into the foyer. Kris is wearing cream-colored pants, a matching Comme des Garçons duster, and Stella McCartney platform sneakers. “We were filming today,” she says. “I was on the other side of the Valley and I rushed home to throw dinner together, and I'm still dressed in this dumb outfit—usually I'm in my sweats and UGGs.”

Kendall is sitting on a bar stool at the island in the kitchen, in the same clothes she had on for our morning drive, acting at first a little sullen, as if she hasn't completely shaken off that teenage-girl-embarrassed-by-her-mom thing. Kris offers to make me a drink and runs through an exhaustive list of options. When I settle on a vodka and orange juice, she mixes me a cocktail so big and fat that I need two hands to lift it to my mouth. “Mom, that glass is huge,” says Kendall. “And it's little full, no?”

“Well, I know, sweetie,” says Kris, “but sometimes we get thirsty.” She laughs. Kendall, who is about to move into a new six-bedroom, $6.5 million house in the Hollywood Hills, is the only member of the clan who has (sort of) moved away—the rest have all bought houses near Mom. We head to the dining room, where there is a very long table, one end set for Kendall and me. A Mariah Carey ballad wafts through the house; there are candles flickering. “I feel like we're on a date,” says Kendall, “and Mom's supervising.”

By the time Kris appears with the main course, I have just asked Kendall what was the worst thing she did as a kid, and now she puts the question to her mother. “She would come to us every night at ten and go, ‘OK, Mom, I'm ready for bed now,’” Kris says. “The perfect child. She never really did anything bad.”

“The only thing I can think of is that I would sneak out at night and go sleep at my boyfriend's house,” Kendall says.

“You snuck out at night? That is so Khloe of you,” Kris says, turning to head back into the kitchen.

“I was more scared of Dad—with boys and stuff,” Kendall tells me. “I was definitely hiding it more from him. But I knew if I told her she might tell him.”

Gender roles in this family, it would seem, are rather baroque at this point. Earlier in the day I had said to Kendall that I got the sense from watching I Am Cait that her mom is tough on her dad. “She's supertough on him,” Kendall had said. “She's tough on all of us, to be honest—she's a mom-ager.”

I ask her what having a parent who's transitioning when you're a teenager does to your sense of sexual or gender identity. “You want to know what's crazy?” Kendall says. “I want to be careful about how I say this because I don't want it to come off wrong, because I've never said this out loud, but I have recently . . . even when I say ‘him’ or ‘her’ about someone who is clearly a guy or clearly a girl—even with my mom—I second-guess it now because of my dad.”

Perhaps because she hasn't had a boyfriend in two years, well, people like to talk. But Kendall says the reason no one knows much about her romantic life is that there hasn't been much to report, because all she does is work—and, again, because she learned the lessons from her sisters all too well. “Why would you let other people have their opinion on it, when you're not even certain of what's going on?” she says. “When you're young, everything's just kind of all over the place. I don't like it when people are all up in my business.”

Kendall is still at that age where the metabolism idles high, which means that she is eating like a teenage boy. She shovels in more pasta and then heads down a path I didn't see coming. “We're very accepting of people and of being different and being who you are,” she says, unbidden. “We're not judgmental. But obviously it's strange having your dad, who was so male, completely reverse. It is definitely a gnarly experience. But my whole life we would, like, catch her, and we would be like, What is going on here? I think we know, but do we? At one point Kylie and I thought he was cheating on my mom, because he had makeup and nail polish. One time we found those squishy boob things. We found wigs. And then one time I actually ran into her. In this house. She had no idea. She would wake up really early just so she could dress up and move around the house and get that little kick for the morning, and then go back to being Bruce—take us to school, totally normal. So one morning I woke up at 4:00 A.M. so thirsty, came downstairs into the kitchen, and grabbed a bottle of water. And as I was coming back out, my dad was coming down the stairs in, like, a wig and makeup and shoes—the full nine. And she didn't see me. I literally froze. Please don't turn left. Because she could either turn left or turn right. Thank God she turned right and—to this day!—has no idea that happened. That was the first time I had ever seen her.” She pauses for a moment. “My mom knew. She knew since their third date.”

Suddenly Kris appears. “Broooowwwwnnnnnieeees!” She sets down plates of freshly baked brownies with a scoop of vanilla ice cream and joins us for dessert.

A couple of weeks later, I meet up with Kendall in Paris, where she has come to walk a Givenchy show. On the night before the show she pulls up to the house's atelier on Avenue Montaigne in a black town car at exactly 9:30 (always on time), the door opens, and she unfolds her long, slender legs like a spider and steps out in a billowy red-plaid jumpsuit with spiky black boots. As we head upstairs she says, “I got here this morning but slept all day. I'm a blur.”

Earlier I had asked Kendall about the best and worst part of modeling. “I don't think that people understand how lonely it can be,” she said. “All you're doing is traveling the world by yourself to do a job and then go back to your hotel by yourself. It's a different life than you imagined.”

Upstairs, Riccardo Tisci appears, and Kendall comes out in the dress she will wear tomorrow. While Tisci sizes her up, several women wearing white lab coats and gloves materialize, speaking French and Italian, and begin to flit around Kendall with pins and tape, making adjustments to the dress at the designer's direction. When Kendall goes away to take off the dress, Tisci says to me, “She's very special.” He had become friendly with Kim and Kanye, he says, but had no idea that Kim had a little sister who was modeling. One day, a casting director showed him some Polaroids. “Oh, my God, she is so beeeuutiful!,” Tisci remarked. “She came to see us. And the casting editor said, ‘You know she is the seester of Keem Kardashian?’ Kendall came completely separate. I promise you. From a Polaroid. We still have it.”

I ask him what he saw in that Polaroid. “What I saw was a beauty that was not a classic beauty—it was beauty, but it was, as well, a coolness. She can look like all the other girls, but without makeup she can look like a really, really young girl from next door. She is literally the American dream of today. She's approachable. Her style is very strong—you can see by the way she puts clothes together; you can see it in the paparazzi pictures. She is always dressed in a cool way. She is the one who started the new era, no?”

The next day, I meet Kendall at Café Marly, an outdoor spot tucked into the arcades near the part of the Louvre that overlooks the glass pyramid. She is wearing another billowy getup, a long, flesh-toned dress with boots that have a flashy seventies disco heel. Suddenly a young girl appears next to Kendall to ask for a selfie, but she is so starstruck she can barely hold the camera. Kendall sweetly takes it from her and snaps the shot. “I love you,” says the girl as she scampers away in tears.

Kendall went out after her fitting last night to the du moment comfort-food joint Ferdi with her friend Virgil Abloh, the designer of Off-White. She got back to her hotel at 1:00 A.M. and slept until she came to meet me here at 2:30 P.M. “I feel like I've been hit by a truck,” she says, sounding neither bratty nor spoiled nor cynical. Indeed, she is resigned to idea that she may be facing years of constant fatigue. “This is a career—I want this to last for a long time,” she says. “Not that I won't venture out and do other things, but I want this to be like a Cindy Crawford thing: I want it to last until I am her age. That's why I love her so much and why I look up to her: Her life now is something that I want my life to be like.”

Kendall isn't using the word supermodel here, but that's what she means. But models don't become household names these days (unless they are also reality-TV stars), and that has largely to do with the fact that the turnover rate has accelerated—people don't really have time to get attached to the girls anymore. And because models love to feed the hungry beast that is Instagram, they tend to burn through their celebrity capital much more quickly; instead of one cover a month, they're now available to the public constantly.

Kendall has met Linda and Christy and Naomi, too, but the reason she admires Cindy is that she has spent time with her family, been to her house a few times. “I love her daughter,” she says. “She's the sweetest and so ridiculously beautiful. She looks exactly like Cindy, minus the mole. It's actually the creepiest but coolest thing ever. That's what I want. A little mini-me daughter? How cute is that?”

“She's not giving her power away,” Crawford says of Kendall. “She's already light-years ahead of where I was at her age. It took me a while to own that.”

If Cindy was the original mogul model, then Kendall and Gigi and Bella—this “new wave of California girls,” as Kim Kardashian West puts it—are taking that approach to a whole other level. “They're killing it,” says Cindy. But what is perhaps most remarkable about Kendall, what separates her from the pack, is that she came to this business as a known quantity—millions have watched her grow up—and yet, even more like Linda Evangelista than like the reliably gorgeous but comfortingly always-the-same Cindy, she has somehow remained magically mutable enough so that designers and photographers and fashion editors yearn to project their visions onto her. It is a rare and elusive gift for a model that cannot be taught or imitated. There can be only one Kendall.

I think she somehow knew that our blissful, camera-free morning in Sherman Oaks couldn't last. As we leave that strange park with the miniature golf courses, Kendall checks the traffic on her phone. The 405 is jammed, so she decides to take Benedict Canyon Drive, a famously steep, windy road that takes you from the Valley up over Mulholland and back down through hairpin turns into Beverly Hills. Just after we crest the peak and start down the other side, though, the engine cuts out. “Something just happened,” she says calmly as she pumps the clutch. “I think we ran out of gas.” So down we go, coasting noiselessly at 50 mph, until we finally come to a side street. Kendall muscles the car around the turn, and we drift to a stop and start laughing. She calls her friend Lauren, who lives nearby, and within minutes Lauren appears in her father's two-seater Porsche convertible and the three of us somehow squeeze in and head to one of the few gas stations in Beverly Hills—where the paparazzi find us. They follow us back to her car, snapping shots from long lenses poking through half-opened windows as Kendall pours gas into her tank from a little red can.

That's the shot that's going to be in the Daily Mail tomorrow, I say.

“I know, right? KENDALL RUNS OUT OF GAS. That's the drama in my life.”

The actual Daily Mail headline the next day: OOPS! KENDALL JENNER'S CLASSIC CAR RUNS OUT OF GAS WHILE ON THE ROAD—BUT THANKFULLY AN OLDER GENTLEMAN COMES TO THE RESCUE. (Ouch.) I tease her that she set the whole thing up to get more attention, and for a second she takes me seriously. “I am not that type of person at all,” she says. It is the only time I hear her sound even vaguely defensive. “I already think this world is so fake. Why would I egg that on any further? It's literally the last thing I would ever want to do.”

She looks at me and suddenly realizes I'm kidding—or am I? Does it even matter? She knows what's real.


In this story: hair, Garren at Garren New York for R+Co and Malcolm Edwards; makeup, Isamaya French. Also featuring set design by Gille Mills for the Magnet Agency and production by Gabriel Hill for Ge Projects.