When you're having lunch with Kendall Jenner, whose presence tends to draw rabid mobs of fans and photographers, it's best to secure the perimeter first.
That is why I arrive well before our meeting at Untitled, in New York City's Whitney Museum of American Art: so I can stake out a private corner table and arrange the chairs to face away from the door. As I'm fussing with my tape recorder, I count eight teenage girls streaming into the museum wearing black chokers—a look lifted directly from Jenner.
Then a lithe brunette—in tiny denim cutoffs, an equally tiny cropped white T-shirt, and a fringed suede vintage jacket—is coming my way. Her glossy hair is swept into a half-up topknot.
She's here? Jenner is known for being punctual, but isn't 20 minutes early a tad extreme? I haven't had a chance to go over my questions—or maybe even get in a quick meditation.
Rattled that she's so early—and so tall—I hit the edge of a plate. It shatters, loudly, on the floor. The entire restaurant goes silent. All heads snap in our direction. There goes discretion.
Jenner sits and looks expectantly at me. She's not one, it seems, for small talk. Even for a 20-year-old, she looks very dewy and fresh despite having gone out with Hailey Baldwin the night before. (It's almost possible, through paparazzi shots, to track her movements in real time.) As she tucks her phone into her bag, I ask to see her screen saver. "It's really obnoxious," she says, gleefully showing me a text bubble that reads "I gave you a boner, don't ignore me."
Jenner is polite and measured, friendly but watchful. Her speech is sprinkled with "like," "literally," and California-isms such as "gnarly." Once the Shy One of the famous Kardashian clan, she could never last the night at a sleepover because she would grow too homesick. "After everyone fell asleep, I'd call my dad, bawling, and he'd say, 'All right, all right, I'm on my way,' " she says.
But this year in particular, Jenner has grown notably more confident. (Maybe you saw a picture of her nipple piercing when she flashed it on the streets of New York City in a sheer black top? "Who cares? Everyone's seen a boob before.") Perhaps it's because her ascent from reality-TV stardom to the pinnacle of the fashion world is now complete. It started at Marc Jacobs's fall 2014 show, when photos of her with edgy bleached brows and a sheer top exploded on the Internet, a move that was strategically planned. ("This is my big kickoff to start and grow my career," she told a reporter afterward.) Later that year, she landed a coveted contract as a face of Estée Lauder; her status was cemented in 2015, when she closed a Chanel show in Paris, walking the runway alone.
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Throughout her rise, Jenner's deft handling of social media has made her arguably the world's most influential model at the moment (she has 18 million followers on Twitter, 61 million on Instagram). Which raises the question: Why are we all so obsessed? For starters, viewers of Keeping Up With the Kardashians have invested nine years in watching her grow up. Despite the public scrutiny, she maintains a crucial bit of mystery and never comes off like she is trying too hard. "I want my Instagram to look good. You go through people's pages and it's all, like, selfies or their butts. I love a good belfie—don't get me wrong," she says. "I post those every once in a while." (Yes, a belfie is a selfie of your butt.)
And of course, she wears clothes beautifully—it's her job. You believe they fit her style, that she's not playing a role, whether or not she is.
It also helps to have an inner circle of glamorous, social-media-savvy friends, including models Gigi Hadid, Cara Delevingne, and Baldwin, with whom Jenner got matching broken-heart tattoos. "This is going to sound really, really lame, but we all call ourselves the Super Natural Friend Group because we all have such cool individual lives and we've been dreaming about them since we were so young," says Jenner, who's fiercely loyal to her coterie. "I'm a Scorpio, so I stick to people. If I love you, I love you. If I don't like you, you're screwed."
Jenner controls her social media, but, significantly, it does not control her. On Twitter, she recently wrote, "Put that away and talk to me"—lyrics to a James Blake song but also her mantra. "I find it offensive if you're with someone at a dinner and they're just sitting on their phone the whole time," she says, leaning forward intently. "I take that personally. Like, am I not interesting enough for you to talk to me? It's so crazy because even though we talk about trying to be present, everyone wants to be in the future now."
She sighs. "I definitely have close friends, and even some family members, who are so connected to their phone and can't get off of it." She recalls a vacation she took with her little sister, Kylie, two years ago. "It was the first time we had ever been to this beautiful place, and we were sitting in a car," she says. "I was just zoning out, taking it all in. And Kylie wouldn't put her phone down. I'm like, 'That's so crazy to me that you're not experiencing this.' That was the moment it kind of clicked for me. And I didn't like it. So sometimes I delete Instagram or Twitter or Snapchat off my phone for a couple days."
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Yet another key to Jenner's appeal is that she's not alienatingly cool. She doesn't really drink alcohol (unless she's "in Europe and it's legal"). She likes to bake cupcakes, cookies, and "insane maple scones from scratch." She prizes neatness. "Oh, I'm ridiculously OCD," she says. "Order gives me a complete feeling, like everything is good."
Then I decide to test her. "What happens," I ask, "if I do this?" I take her napkin, crumple it, and toss it next to her plate. She eyes it uneasily for half a second. "I have to fix it," she mutters, then snatches it up and refolds it into a crisp, professional-looking rectangle.
Along with being shy, Jenner maintains that she was easily the "most awkward" of the Kardashian girls. "I'm superawkward," she says. She glances down at her lap. "I mean, the way I'm sitting right now is pretty awkward." We both notice that we're slumping and straighten up.
Jenner seems pretty poised to me. While I feel tense that a patio full of outdoor diners is gawping at us through the café windows—I use the term "us" loosely here—she is serenely unconcerned. In fact, the only time in our conversation that her composure drops is when I inquire about her love life—according to reports, she is seeing rapper A$AP Rocky. Her faltering response resembles any 20-year-old explaining that it's, you know, complicated.
"I just—my personal life, I'm so young," she says, fiddling with her hair. "Whoever I'm dating, or going to be dating, is young, too. So I don't think it's figured out. Do you know what I mean? So if I don't know what it is, I'd rather not let everyone else know."
A text pings. This is one she has to get—it's from her agent. Jenner is due at an Allure video shoot, and as I now know, she will not want to be tardy.
Lately she has been working nonstop; she recently found her first gray hair and attributed it to stress. "I'm off all next month, though," she adds, heading off any impression that she is complaining. She gives me a firm handshake and heads for the door.
The paparazzi are amassing outside the museum as Jenner slips expertly through the crowd and quickly ducks into a waiting car. By the time most onlookers try for a glimpse of her, she is gone. Fortunately for them, photos of her dash to the curb appear online within the hour.
Fashion editor: Rachael Wang. Hair: Jimmy Paul. Makeup artist: Romy Soleimani.
