Kendall Jenner Is In Her Feelings for Vogue’s June/July 2024 Cover

At first glance, there was nothing atypical about the photos Kendall Jenner shared following her New Year’s trip to Barbados: of string bikinis and gauzy dresses, palm trees in silhouette against sunsets, wine glasses clanking, fireworks popping. But if you were searching for a dissonant note, you might find it in the copy of The Year of Magical Thinking, Joan Didion’s wrenching 2005 memoir of grief and loss, splayed on the green canvas of Jenner’s sun lounger.

“Somebody said, ‘Damn, that’s a beach read for you?!’ ” she recalls. “I would read a few pages on the sand, and then my friends would come out and they’d be like, ‘Take a shot!’ ”

A meditation on the peculiar tricks an imagination may play to avoid a goodbye surely chafed against the spirit of the party weekend. But such mental toggling is classic Kendall Jenner. The heavy stuff bubbles up to the point of overflowing, and that’s when friends and sisters and horses and other salves come to the rescue. “It’s kind of interesting that we’re wired to not think about death all the time,” Jenner muses. “And yet we don’t know the concept of never-​ending. We can’t visualize a never-ending universe, but at the same time, nothing scares me more than the end of something. I’m so bad at goodbyes.” She catches herself and starts to laugh. What better defense against the dark than humor? “These are the thoughts that creep into my mind. I can’t let myself get too deep into them, or else I spiral.”

Such is the tenor of the chatter one day in early spring on Jenner’s back patio, in her home in a gated enclave at the crest of Beverly Hills, halfway between the twin fulcrums of her life: Calabasas (her hometown) and Los Angeles International Airport. The sky is a blue that occurs in Los Angeles only after the rain has rinsed the atmosphere of all man-made assaults. A month earlier, a mudslide landed in and was essentially contained by her swimming pool, though a breeze seen in the surface ripples and heard in the fruit trees and palms has made this a distant memory.

Mud in the water is an apt metaphor for that habit of mind that has been Jenner’s burden since she was a little girl. “I’m a negative thinker,” she says. “That’s my problem. I’m always worrying about something that may never happen.” Sunshine filters in wide stripes through the dark wooden pergola above us, but there is a chill in the air, and Jenner sits with her knees up and her legs tucked completely inside a giant gray wool sweater from The Row. (“I don’t wear anything else,” she says, exaggerating, though street style observers can confirm that Jenner has made a decisive shift into quiet luxury these last months.) She sees no reason not to say plainly that I have caught her in the middle of a rough patch. “I don’t see why I shouldn’t be honest about it. In my career right now I feel really stable, really hopeful. But I’ve had a tough two months. I haven’t been myself, and my friends see it. 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. That’s life—I’m always going to be in and out of those feelings. In past interviews, when someone’s asked me about my mental state, it’s always been, ‘I’m great right now, but this is what I’ve dealt with.’ Well, right now I’m actually in it.”

Because Jenner developed in the great Kardashian public image incubator, habitually in front of the camera since Keeping Up With the Kardashians premiered when she was 11 (now simply called The Kardashians), she is a master of the art of talking about feelings while distilling out the facts that might have shaped them. Boyfriends? Breakups? She knows much better than to go there. “Let’s just say it’s personal-life-journey stuff,” she says. “I’m a stresser and a control freak by nature. I’ll thank my mom for that one. This is also kind of a transitional period for me. I’m 28 now, and I think I’m in my Saturn return.” (For the astrologically uninclined, Saturn, which revolves around the sun every 29.5 years, is the planet of wisdom and personal responsibility, and so a Saturn return involves the shaking off of external influences such as parents, teachers, and bosses, and becoming superintendent of one’s own life.) “I’m so tired emotionally, but I think it’s good. It’s almost like I’m purging something for my 30s. That’s my theory.”

If transitions sound a little bit like goodbyes, it’s no wonder Jenner should find herself psychically wobbly. This year marks her 10th anniversary as a model, a time for celebration and also, perhaps, recalibration. Though there was assorted juvenilia—a Forever 21 campaign, covers of American Cheerleader and Teen Prom—Jenner regards landing Marc Jacobs’s fall 2014 show as the true beginning of her career. Eyebrow-less, bewigged, in a sheer brown V-neck T-shirt that left no nipple to the imagination, she was as anonymous as her already operational fame permitted. “I really went into that season thinking, I don’t know how this is going to go, but I’m just going to try,” she recalls. “Then I booked Marc Jacobs, and I thought, Cool, if this is all I get, I can go home happy.” Then Riccardo Tisci of Givenchy called. And soon after, Chanel. “That was kind of like, What the fuck? This is crazy. This is actually happening. I remember the excitement and the disbelief of that time. And from there the takeoff was really fast.”

In a fickle business, her power has proven uncommonly durable; Jenner is the world’s highest paid model for six years running. And while her family’s celebrity may have provided entrée, or at least invited curiosity, it was not an unalloyed advantage. Back then, the Kardashian name evoked either a luxe-suburban vapidity or a meretricious Hollywood style, neither of which had the warm embrace of the fashion atelier. Marc Jacobs remembers having to rise above that initial skepticism when the stylist Katie Grand, his longtime collaborator, suggested he meet Jenner.

“Katie knew me well enough to know that I wasn’t excited by the Kardashian fame,” he explains. “I just wasn’t, to be very honest. I was aware of who they were. There was no judgment. But I have a job to do, a fashion show, and that means finding models who can show the clothes the way I think they should be shown. That show was very much about the uniformity of the cast. Some are more about individuality and maybe exaggerating different models’ features and personalities. But in this one there was this almost narcotic-like pull to the thing. It was this army of the same person. Kendall couldn’t be Kendall Jenner at all. It was really about anonymity—which is kind of ironic, and that irony appeals to me.”

It appealed to Jenner too because she was so eager to prove people wrong. “I think they didn’t believe in me when I came into the industry. That’s been a constant narrative in the hater world online, and at times that’s been really hard,” she acknowledges. “But I always say, I like being a pleasant surprise. I like that motivation in a way—like, Oh, you thought? You thought! Fashion is always shifting. There are always new vibes and energies. When I came into it, you didn’t really see quote-unquote famous girls. Cara Delevingne was probably the biggest one who was known outside of modeling. She opened that door for me, and from there it blew up into a whole new thing. Now there’s another vibe coming through. You’re seeing a lot of social media creators at the shows. It’s great. It’s always just shifting and changing, and you take it day by day. I suss out the vibe. Does it align with me? If it still does, great. You don’t know what’s around the corner.”

Jacobs feels that while some designers look to leverage the fame of their models, as has lately occurred with the reappearance on runways of the ’90s Supers, there is a real risk that the clothes themselves will disappear beneath those outsize auras. (Addressing this distortion, Jacobs’s fall 2024 show had models walk among an oversized table and chairs by the artist Robert Therrien, as if to make them small again.) “When you put Kendall or Kaia or Gigi or Bella in a show, you can expect that most of what you will read online the following day is about those four people being in the show,” he says. “You will know very little about the collection. I think that’s problematic. But this idea of a personality as a great model is just where we’re at. What might have been the story in the 1970s, with a Lauren Hutton, who started off as a model and became super well-known as a model—now things are different. I think Kendall’s beautiful. She wears clothes with confidence. I think she’s also super nice and charming. She photographs well. She has all the things, but then also this thing that makes her very of this moment, this reality-celebrity thing. There are two ways you can deal with that. You can say, I don’t want anything to do with this, or say, This is real and I can embrace it. I think that’s the way you go with Kendall.”

Jenner and her sister Kylie grew up in a vast blended family that included eight older half-siblings. The shyest of the brood, she was perhaps the least temperamentally equipped for life on the reality show that her mother, Kris, pitched to Ryan Seacrest in 2007. She liked to be alone, she liked to ride horses, and she struggled to make inroads with her peers. Watching Kylie, two years younger, move so easily among her friends was sometimes painful. Jenner believes she has suffered from anxiety since she was seven years old, though back then she didn’t have a name for the feeling. She often approached her mother complaining of difficulty breathing, and Kris found it hard to reassure her. Doctor visits ensued, and she would invariably check out fine. “I was an emotional kid, always in my feelings and my head,” she remembers. “I freaked myself out a bit.” She learned much later that those boom-out-of-nowhere bursts of dread, accompanied by a mix of physical symptoms, were panic attacks.

Fashion cured her of her shyness, as she hoped it would. “I remember being that awkward kid at the beginning of my modeling career and thinking to myself, I’m going to come out of this,” she says. “It’s such a social job—working with photographers and stylists and creative directors all day long—and that’s how things started to click for me. I tend to get really emotional now talking about my friendships. I still find myself standing at the edge of a conversation at a big social event, but now I have the most incredible friend group, and as a kid I just didn’t have that. I’m huge on the people in my life. I love getting to know people, I love holding on to people from my past. I’m completely the opposite of the super-shy kid that I was.”

But a year or two into her modeling career, the panic attacks returned. Air travel, that bane of those who hate to cede control, seemed to invite them. “I remember having these meltdowns on planes,” she says. “They would come out of nowhere. I’d be like, Oh my God, oh my God, something’s wrong with my heart: palpitations, shortness of breath, dizziness, double vision, tingles. The whole thing. I’d call my mom hysterically crying and say, ‘I need them to stop the plane, I need them to turn around.’ ” In the years since then, Jenner has built a formidable arsenal in defense of her well-being: deep breathing, distraction, meditation, journaling, weekly psychotherapy, periodic consultations with a spiritual healer. It’s now been two years since her last panic attack.

“Kendall is somebody who really cares about growing and knowing herself better and going deeper with herself,” her best friend, Hailey Bieber, explains. “I really respect that about her. We’re not stingy with each other when it comes to sharing the stuff we’ve done or learned or tried, whether that’s cold plunges or saunas, a really cool naturopath, a new skin-care product or supplement, a trainer, or somebody who does sound baths. It’s nice when your friend is as into taking care of herself as you are, and we share a little black book of wellness contacts.”

But surviving an onslaught of arrows that fly daily through the tiny holes in her self-esteem has proven more difficult than mere stress management. Jenner has an old and uneasy relationship with “the haters.” She remembers a moment years ago, in the early days of Keeping Up, when her sister Khloé gave her some advice about how to navigate social media: “She said to me, ‘You’ll scroll through comments and you’ll see a kajillion I love you’s, you’re great, you’re so pretty, you’re the best. And the one comment that’s not nice is the one you’re going to harp on.’ It’s so true. They’re just so…loud. But why do we fixate on these? Are they a projection of our own insecurities? A huge thing I work on in therapy is feeling worthy of where I’m at and knowing that I can’t let what’s being said about me on the internet, especially about my worthiness, get in my head too much. I let it get there, and I think that’s what brings me down a lot of the time.”

Jenner doesn’t particularly believe the hype about Kendall Jenner. And while this might serve to keep her grounded, it also tends to play into that well-worn worry: Does she deserve to be on that cover, in that dress, next to that man, or whatever it is that piques her detractors on a given day? “I do have that impostor syndrome of, like, Wait, this is all happening to me? What did I do to deserve it?” Someone once told her that anxiety cannot exist in gratitude. This clicked for her, and it’s something she tries to keep constantly in mind. “I think I’m one of the luckiest girls in the world, and I appreciate every one who has decided to follow me”—some 294 million on Instagram as of last count—“but I also sit there and I’m like, I feel so regular.”

In these recent doldrums, Jenner confesses to abandoning what for her is a first principle when it comes to her mental health. Cognitive behavioral therapists call it behavioral activation, which essentially means doing the things that experience has shown you will make you feel better. “This is one of those times when I feel I’m actively not protecting myself or actively doing things that I know are hurting me,” she explains. “That’s such an important part of my wellness: recognizing those moments and saying, Stop! It’s not one-size-fits-all, but for me, getting out of bed in the morning and putting one foot in front of the other is so helpful for me. Moving, getting my blood flowing. When I say I’m struggling right now, I’m not doing those helpful things. Choosing to sit in my bed and mope all day is setting myself up for failure.”

But this is the paradox of behavioral activation: The times when it’s most important are the very times when it’s hardest to muster. Jenner believes in the interdependence of thoughts, feelings, and behavior, the classic cognitive triad of CBT. Recently she bought a little book she found on TikTok, Joseph Nguyen’s Don’t Believe Everything You Think, that has helped her to think more positively so that she can go out and act more positively. And for Jenner, no activity nourishes her quite like riding her horses, the great pastime of her childhood that fell into remission in the first flush of her career but returned when the demands of work left her brittle and exhausted. She now keeps two jumpers, Dylandra and Lady Bird, at a stable in the deep San Fernando Valley. Her trail horse, Arizona, lives in Hidden Hills near her mother and sisters. And a foal, Copernicus, which she bred herself, is kept in Santa Barbara until he is old enough to train. She calls it a “healthy addiction,” but the fact that horseback riding was her first passion is crucial to its power.

“I always encourage anyone, especially my friends, to pick up something they loved doing as a kid,” she says. (With this in mind, Jenner recently encouraged Bieber, who was a serious ballerina in childhood, to return to ballet class.) “Whenever I go ride, of course it’s a great excuse to get outside and not be on my phone and forget about work and fully put my brain and my energy into how I’m going to get my horse over these obstacles. But there’s something about the nostalgia of it. I liked this so much as a kid, but as a kid you’re working with a trainer, and your parents won’t get you the helmet or the crop you want. Now I’m an adult and it’s all my choice and I can do all this for myself. It’s like soul food for me. I loved this as a kid. It was something I did every day that I could. I was obsessed, like—boys who? I feel like my kid self when I’m out there.”

Responsibilities, compromises, Saturn return, and all that—there is no lasting escape from the weight of adult life. But there are refuges, and for Jenner, accessing her childhood self has become a cornerstone of her care routine. “In therapy you talk about your childhood,” she says, “and I have an exercise that I do where I have pictures of me as a kid pasted on my bathroom mirror, and if I start to speak poorly to myself, I go talk to her. If someone’s treated me poorly and I’m taking it too hard, I go look at her and I’ll say, I’ll never let this happen to you again. I talk to her, like a freak.” She laughs. She knows it sounds corny. “It’s the same concept with riding. I’m doing it for her. I still love it, but she just loved it so much. It’s all she cared about, and in the moment it’s all I care about. There are so many big, bad, scary things to deal with when you’re an adult. As a kid, if you told me I couldn’t go ride, it was the end of the world.” I ask if she’s found a way to prevent the world from ending, after all. “Yes! That’s it!”

Kris Jenner likes to tell the story of how she invited Russell James, the fashion photographer closely associated with Victoria’s Secret, to her house one day to meet Kendall when she was about 15. Kris is unabashed about her stage-​mothering, and she credits James for setting her daughter’s early career in motion. “Kendall decided very young exactly what she wanted to do, and it kind of became my mission to help her get there,” she explains. “So I told her, ‘Put on your prettiest party dress and put a big bow in your hair,’ like I always did. Instead Kendall came walking down the double staircase in the skinniest jeans, the biggest heels, her hair all messy. Kendall did Kendall, and the rest is history.”

To have spent nearly a decade at the pinnacle of modeling is a special feat; Jenner had no grand plan to achieve it and has no plan to keep it going. She surveys the landscape, sees other women she thinks are doing it better, and feels okay about it. She is competing with no one but herself, she insists. “Growing up with sisters, you would think it would be the opposite,” she says. “Even with my little sister—the biggest thing we would fight over was the TV remote. There was never that who’s-better-dressed, who’s-prettier thing. It was always: You’re you, I’m me. I’ve never thought of my career as a competition, and that’s thanks to awesome sisters. I really do me, and if you don’t like it, that’s okay. But I trust that me being the most authentic version of myself will get me to the places it needs to get me.”

Jenner still loves modeling, but her priorities have shifted somewhat. A few years ago, she launched 818 Tequila, and she has relished the quite different role it offers, in which she must consider how her leadership affects the morale of a growing team. (“I did not see this one coming,” Kris says.) Inevitably, the pressures of a new business have compelled her to be more particular about the fashion opportunities she entertains. “It’s a privilege to be able to say no,” she says. Meanwhile, she can’t help watching models from the eras that preceded hers bob in and out of fashion and wondering how best to make use of the next decade or two. “The first 10 years went by so fast, and the second 10 will go even faster. There are so many women who are older than me who still model at a really high level. I look at people like hot-ass Cindy Crawford and hot-ass Christy Turlington, and they’re still as gorgeous as ever and having fun with it. Mariacarla [Boscono] is fucking bomb. She’s never looked better. I think that that’s only exciting for me, and empowering for me to see women older than me who are smashing it.”

Turlington, whom she has never met, holds especial fascination—not only as “the most gorgeous woman to ever exist,” as Jenner puts it, but as a supermodel who somehow seemed to float above or apart from the world she inhabited, and who, when it was time, drifted away to focus on education, fashion, and philanthropy. “I spent a lot of time looking at her face as a kid,” Jenner recalls. “She seemed so calm and collected. I really appreciated her energy through it all. And it feels like life outside modeling and family were really important to her. Relationships mean so much to me, and I can’t wait to have a life with someone one day, to have kids, to create a family. Christy just gives good vibes. Maybe she cared a little bit less! I think that’s really cool.”

Jenner is now the only daughter who isn’t a mother herself and the only one who does not live within walking distance from her mother’s home. She didn’t exactly intend to create a boundary when she bought a house in the city almost seven years ago. “But I always am,” she explains. “Even as a kid, I always have been. There are days when I look at what they have and think, That’s really special. I do like being a little bit removed, but one day I’ll make my way, probably. When I was young I used to say that by 27 I’d love to have kids. Now I’m past that and I feel like I’m still so young. I’m enjoying my kidless freedom.”

When the world really does seem to be your oyster, when possibilities professional, romantic, and otherwise abound, how do you find that very personal equilibrium, somewhere between all of it and none of it? Jenner is a poster girl for the all-of-it generation, of lives lived globally, of working hard and playing hard from Aspen to the Super Bowl, from the Vanity Fair party to Easter luncheon at Mom’s house. This evening, Jenner has a fitting for an upcoming trip to Paris; tomorrow morning, therapy at 8, a phone meeting at 9, and a press junket for the fifth season of The Kardashians immediately afterward. How much longer will she submit to the reality show cameras? “It’s not my biggest cup of tea,” she admits. “And to be honest, I’ve never been very comfortable filming. I just feel I’m not good at it.” She’s grateful for the family time the show creates—but if it were up to her, off-duty hours would simply be spent hanging at home, whether that means getting in bed early with a TV show or inviting a crew over to drink some tequila and watch a basketball game. Jenner has talked before about making every moment count. A nice idea, to be sure, but one she’s not convinced she believes in.

“It’s really real to say that not every day is a magical day,” she offers. “Sometimes the reality of life is that you’re just chilling. If it’s a Sunday and you have nothing to do and no one calls you, let’s please enjoy that as well. People think that life has to be these massive moments, and especially with social media, life is presented by a lot of people like, All these amazing things are happening to me and I’m doing it all! No. This is something I have to remind myself. Not every day is meant to be the party. Some days are meant to be the chill.”