At first look, Kendall Jenner’s images from her New Year’s trip to Barbados appeared typical: string bikinis and gauzy skirts, palm palms silhouetted against sunsets, wine glasses clanking, fireworks blasting. If you were looking for a discordant note, you may find it in The Year of Magical Thinking, Joan Didion’s devastating 2005 memoir of grief and loss, which is smeared across the green canvas of Jenner’s sun lounger.
“Somebody said, ‘Damn, that’s a beach read for you?!'” she recalled. “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 strange tricks the imagination may perform to avoid saying goodbye certainly went against the spirit of the party weekend. However, Kendall Jenner is known for her mental gymnastics. The heavy thing rises up to the point of overflowing, then friends and sisters, horses, and other salves arrive to help. “It’s kind of interesting that we’re wired to not think about death all the time,” Jenner says. “We don’t understand the concept of never-ending.
We cannot imagine an infinite cosmos, but nothing scares me more than the end of something. I’m really horrible at saying goodbye. She catches herself and begins to chuckle. What better way to combat darkness than via humor? “These are the thoughts that come to my head. I can’t get too deep into them, or I’ll spiral.”
“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.”
Such was the tone of the conversation 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 her life’s twin fulcrums: Calabasas (her hometown) and Los Angeles International Airport. The sky in Los Angeles turns blue only after the rain has washed away all man-made attacks. A month ago, a mudslide landed in and was largely contained by her swimming pool, but a breeze seen in the surface ripples and audible in the fruit trees and palms has made it a distant memory.
Mud in the water is a fitting metaphor for Jenner’s mental habit, which she has carried with her since she was a child. “I’m a negative thinker,” she admits. “It’s my problem. I’m constantly fretting about something that might never happen.” Sunshine filters in wide stripes through the dark wooden pergola above us, but there’s a chill in the air, so Jenner sits with her knees up and her legs entirely tucked into a massive gray wool sweater from The Row. (“I don’t wear anything else,” she exaggerates, but street style observers can corroborate that Jenner has made a clear shift toward understated luxury in recent months.)
She finds no reason not to express unequivocally that I have caught her in the thick of a tough patch. “I can’t see why I shouldn’t be open about it. I am currently feeling really solid and hopeful about my career. But I’ve had a rough two months. I haven’t been myself, and my friends notice. I’m sadder than usual. I’m much more anxious than normal. So I’m not going to sit here and act like everything is fine. That’s life—I’ll always be in and out of those emotions. In previous interviews, when asked about my mental state, I’ve always said, ‘I’m fine right now, but this is what I’ve dealt with. Well, I’m now in it.”
Kendall Jenner
Jenner is a master of the art of talking about feelings while distilling out the facts that may have shaped them because she grew up in the great Kardashian public image incubator, having been in front of the camera since the premiere of Keeping Up With the Kardashians when she was 11 years old. Boyfriends? Breakups? She knows better than to go there. “Let’s just say it’s personal-life-journey stuff,” she replies. “I’m a stressor and control freak by nature. I’ll thank my mother for that one.
This is also a bit of a transition phase for me. I’m 28, and I believe I’m in my Saturn return. (For the uninitiated, Saturn, which orbits the sun every 29.5 years, is the planet of wisdom and personal responsibility, so a Saturn return entails letting go of external influences like parents, teachers, and bosses and becoming the superintendent of one’s own life.) “I’m exhausted emotionally, but I believe it’s healthy. It’s almost as if I’m purging for my thirties. “That is my theory.”
If transitions sound like goodbyes, it’s no surprise Jenner is experiencing psychic instability. This year marks her tenth anniversary as a model, a moment for celebration and, possibly, recalibration. Though there was some juvenilia—a Forever 21 campaign, covers of American Cheerleader and Teen Prom—Jenner considers landing Marc Jacobs’s fall 2014 show to be the genuine start of her career. She was as incognito as her already operating renown would allow, browless, bewigged, and dressed in a sheer brown V-neck T-shirt that left no nipple to the imagination.
“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 says. “Then I booked Marc Jacobs, and I thought, Cool, if this is all I get, I can go home happy.” Then Riccardo Tisci from Givenchy called. Soon after, Chanel. “That was sort of like, What the fuck? This is ridiculous. This is actually happening. I remember the excitement and amazement at the moment. From there, the takeoff was really fast.”
In a volatile industry, Jenner’s power has proven unusually enduring; she has been the world’s best paid model for six years in a row. And, while her family’s prominence may have offered entrée, or at least piqued interest, it was not an absolute advantage. Back then, the Kardashian name conjured up images of luxe-suburban vapidity or meretricious Hollywood flair, neither of which possessed the warm embrace of a couture atelier. Marc Jacobs recalls having to overcome his first reluctance when stylist Katie Grand, a longstanding colleague, suggested he meet Jenner.
“Katie knew me well enough to know that I wasn’t excited by the Kardashian fame,” he says. “I simply wasn’t, to be honest. I was aware of who they are. There was no judgment. But I have a job to complete, a fashion show, and that involves selecting models who can represent the garments in the manner I believe they should be. That show was heavily focused on the cast’s uniformity. Some are more about individualism, possibly exaggerating distinct models’ characteristics and personalities. But this one had a narcotic-like pull to it. This was the same person’s army. Kendall could not be Kendall Jenner at all.
It was all about anonymity, which is hilarious and appealing to me.”
It also appealed to Jenner because she was anxious to prove others wrong. “I guess they didn’t trust in me when I first entered the industry. That has been a continual theme in the online hater community, and it has been extremely difficult at times,” she admits. “But I often remark that I enjoy being a nice surprise. In some ways, that drive appeals to me—like, Oh, you thought? You thought! Fashion is constantly altering. There are always fresh vibrations and energy. When I first started out, there weren’t many famous girls. Cara Delevingne was probably the most well-known outside of modeling. She opened that door for me, and it exploded into something entirely new.
There’s another vibe coming through. There are a lot of social media creators at these shows. It’s great. It’s continuously shifting and changing, so you take it day by day. I figure out the feeling. Does it agree with me? If it still works, amazing. You have no idea what’s around the corner.”
Jacobs believes that while some designers seek to capitalize on their models’ prominence, as has recently occurred with the reappearance on runways of the ’90s Supers, there is a genuine risk that the clothing themselves will be overshadowed by such outsized personalities. (To address this distortion, Jacobs’s fall 2024 show had models walking around a huge table and chairs by artist Robert Therrien, as if to shrink them back down.) “When you put Kendall Jenner 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,” according to him. “You’ll know little about the collection.
That seems worrisome to me. However, the idea of a personality as a fantastic model is where we are right now. What would have been the case in the 1970s with a Lauren Hutton, who began as a model and rose to prominence as a model—things have changed. Kendall Jenner is very attractive in my opinion. She wears her clothes confidently. I think she is also quite nice and charming. She takes good photos. She has everything, but she also has this thing that defines her as a reality-celebrity. There are two approaches to deal with this. You can say, “I don’t want anything to do with this,” or, “This is real, and I can accept it.” I think that’s the way to go.
Jenner and her sister Kylie grew up in a large blended family with eight elder half-siblings. She was the shyest of the brood and possibly the least temperamentally suited to life on the reality program that her mother, Kris, pitched to Ryan Seacrest in 2007. She preferred solitude, enjoyed horseback riding, and struggled to connect with her friends. It was occasionally heartbreaking to watch Kylie, who was two years younger, walk so freely among her friends. Jenner feels she has had anxiety since she was seven years old, although she did not know what it was called at the time.
She frequently approached her mother, complaining of trouble breathing, and Kris struggled to soothe her. She visited the doctor several times and was always well. “I was an emotional kid, always in my feelings and my head,” she recalls. “I freaked myself out a bit.” She discovered much later that the sudden bursts of dread, followed by a variety of physical symptoms, were panic attacks.
As she hoped, fashion helped her overcome her timidity. “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 recalls. “It’s a really social job—working with photographers, stylists, and creative directors every day—and that’s when things started to click for me. I get quite emotional when I talk about my friendships these days.
Even with my amazing buddy circle now, I still find myself on the periphery of conversations at large social gatherings; as a child, I simply didn’t have that. I value the people in my life greatly. I enjoy making new friends and maintaining relationships with folks from my past. I’ve come a long way from the extremely bashful child I was.
But after a year or two of modeling, she started having panic episodes again. Air travel appeared to entice them, the scourge of people who detest giving up control. She explains, “I had these meltdowns on planes.” They would appear out of the blue. I would feel as though there was something seriously wrong with my heart: palpitations, breathlessness, lightheadedness, double vision, and tingling. everything about it. I would sob uncontrollably and phone my mother, pleading with her to “stop the plane and turn around.”
Since then, Jenner has gathered an impressive toolkit to protect her health: writing, deep breathing, diversion, meditation, weekly psychotherapy, and sporadic sessions with a spiritual healer. Two years have passed since her last panic attack.
Hailey Bieber, Kendall Jenner best friend, says, “Kendall is somebody who really cares about growing and knowing herself better and going deeper with herself.” “I genuinely admire that quality in her. When it comes to exchanging experiences, knowledge, and products, we don’t hold back when it comes to one another. This includes anything from new skin care products or supplements to cold plunges or saunas, trainers, naturopaths, and sound bathing. When your friend shares your interest in self-care and you have a little black book of wellness connections, that’s lovely.
It has proven more difficult for her to survive the daily barrage of arrows that fly through the little wounds in her self-esteem than it has to just manage her stress. Jenner’s relationship with “the haters” is longstanding and tense. She recalls an incident from when Keeping Up was just getting started and her sister Khloé gave her some tips on how to use social media: “You’ll scroll through comments and you’ll see a kajillion,” she told her. You’re the best, I adore you, and you’re so beautiful. You’ll focus all of your attention on the one rude statement.
That is really accurate. They simply are too noisy. However, why do we obsess over these? Do they reflect our own fears back to us? Feeling worthy of where I am and understanding that I can’t let things that others say about me online—especially regarding my deservingness—get too much of a mental tug are two major things I concentrate on in therapy. I believe that’s what gets to me most of the time because I let it get there.
Jenner doesn’t think much of the Kendall Jenner hype. It also tends to feed into her well-worn concern of whether she deserves to be on that cover, in that clothing, next to that man, or whatever it is that irritates her critics on any given day. All of this may help to keep her grounded. “I do get the impostor syndrome, where I wonder if I’m really experiencing this. What action did I take to earn it?
She once heard that gratitude cannot coexist with anxiety. She found resonance with this and makes it a point to remember it all the time. With 294 million followers on Instagram as of the last count, “I think I’m one of the luckiest girls in the world, and I appreciate every one who has decided to follow me,” she said. “But I also sit there and I’m like, I feel so regular.”
Jenner admits to letting go of what she views as her first principle when it comes to her mental health during these recent downturns. Behavioral activation, as defined by cognitive behavioral therapists, is essentially acting on what your experience has taught you will help you feel better. “It’s one of those moments where I feel like I’m intentionally hurting myself or not actively protecting myself,” she says.
“Stop! That’s such a crucial component of my wellness: acknowledging those moments! While there isn’t a one-size-fits-all solution, for me, getting out of bed in the morning and moving forward with my life is really beneficial. I’m moving, my blood starting to flow. When I say I’m having trouble right now, I’m not acting in that constructive way. I’m setting myself up for failure if I spend my days moping in bed.
However, this is the paradox of behavioral activation: it is most difficult to mobilize at the exact moments when it matters most. Jenner subscribes to the traditional cognitive triad of CBT, which holds that thoughts, feelings, and action are interdependent. She recently purchased Joseph Nguyen’s Don’t Believe Everything You Think, a tiny book she discovered on TikTok, which has encouraged her to think optimistically so that she can act favorably in the outside world.
And for Jenner, nothing nourishes her quite like riding horses—the great childhood hobby that faded during her early career years but reappeared when work expectations left her brittle and drained. She now maintains a stable in the deep San Fernando Valley with two jumpers, Dylandra and Lady Bird. Arizona, her trail horse, resides in Hidden Hills close to her sisters and mother. Additionally, she breeds a foal herself named Copernicus, who is raised in Santa Barbara until he is old enough to begin training. Although she refers to it as a “healthy addiction,” the fact that riding horses was her initial passion is what gives it its strength.
“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.”
She says, “I always encourage anyone to pick up something they loved doing as a kid, especially my friends.” (In light of this, Jenner recently pushed Bieber, who trained as a serious ballerina in her early years, to enroll in ballet classes again.) “Obviously, going for a ride gives me a perfect reason to get outside, put my phone away, forget about work, and focus all of my mental and physical energy into figuring out how to get my horse over these challenges. However, there’s something about its nostalgia.
When I was younger, I really enjoyed this, but you had to work with a trainer and your parents won’t get you the helmet or the crop you want when you’re a kid. I can now make my own decisions and take care of myself as an adult. For me, it’s like soul food. As a child, I adored this. I tried to do it every day that I could. I was so into it, like, which boys? When I’m outside, I feel like my younger self.”
It is impossible to truly escape the burden of adulthood—responsibilities, compromises, the return of Saturn, and all that. However, there are havens, and Jenner’s care regimen now revolves around connecting with her younger self. “In therapy, you talk about your early years. I have an exercise where I put old photos of myself on my bathroom mirror and talk to her if I start talking badly to myself.” I look at the person who has mistreated me and tell her, “I’ll never let this happen to you again,” if I’m taking it too personally. I converse with her in an odd way. She chuckles. She is aware of its corniness.
Riding is similar in that regard. For her, I’m doing this. She just loved it so much, but I still adore it. That was all that mattered to her, and right now, it’s all that matters to me. As an adult, you have to deal with a lot of huge, horrible, scary things. When I was younger, it meant the world to me if you told me I couldn’t go riding. I inquire as to whether she has, in the end, managed to stop the world from ending. Indeed! That concludes it.
Kris Jenner frequently recounts the tale of how, when Kendall Jenner was around fifteen, she invited fashion photographer Russell James, who was closely connected to Victoria’s Secret, to her home one day. Unapologetically admitting to being a stage mother, Kris attributes her daughter’s early career to James.
“Kendall Jenner made her career decision at a young age, and it became my mission to support her in achieving her goals,” the woman says. “So, as usual, I told her to put on her most beautiful party dress and wear a large bow in her hair. Rather, Kendall arrived by means of the double staircase, decked up in the tightest jeans, the highest heels, and disheveled hair. It’s history that Kendall did what Kendall did.
It is a remarkable accomplishment for Kendall Jenner to have lasted almost ten years at the top of the modeling world; she had no huge plans to get there and no plans to stay there. Looking around, she sees other women who seem to be doing it better, and she’s OK with that. She is adamant that she is competing only against herself. “You would think it would be the opposite growing up with sisters,” she explains.
“Even with my younger sister, the TV remote control was the main source of our arguments. That competition between who was prettier or better dressed never existed. Always, it was this: I’m me, you’re you. I attribute my lack of thinking of my career as a competition to my amazing sisters. It’s okay if you don’t like who I actually am; I truly do me. However, I have faith that by being the most genuine version of myself, I will arrive to the right destination.
Jenner’s priorities have changed a little, but she still loves modeling. She started 818 Tequila a few years ago, and she has enjoyed the somewhat distinct role it gives, where she has to think about how her leadership impacts the morale of a developing team. Kris comments, “I did not see this one coming.” She has naturally been forced to be pickier about the fashion prospects she considers due to the demands of a new firm. “Having the ability to say no is a privilege,” she claims. She finds herself thinking how to make the most of the next decade or two while she watches models from earlier eras come and go.
“The first ten years have flown by, and the next ten will fly by even quicker. There are a ton of ladies much older than me who are still very successful models. I see hotties like Christy Turlington and Cindy Crawford, who are both ridiculously attractive and seem to be enjoying themselves. Mariacarla Boscono is an incredible woman. Never has she looked better. The fact that there are women older than me who are succeeding excites and empowers me.
She has never met Turlington, who fascinates her particularly because, in Jenner’s words, she is “the most gorgeous woman to ever exist” in addition to being a supermodel who, at the appropriate time, drifted away to concentrate on philanthropy, fashion, and education. Turlington also seemed to float above or apart from the world she lived in. When Jenner was younger, “I used to spend a lot of time staring at her face.”
She gave off an air of composure. Her energy was really appreciated by me throughout. She seems to have placed a great deal of importance on her family and life outside of modeling. I love relationships so much and I can’t wait to start a family, have children, and live a life with someone. Christy simply exudes positivity. Perhaps her concern had lessened little! That seems extremely awesome to me.
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.
In a situation where opportunities both romantic and professional seem endless, how can you strike a very personal balance between taking advantage of everything and nothing at all? Jenner is the epitome of the all-American generation—one that lives its life on the road, from Aspen to the Super Bowl, from the Vanity Fair party to the Easter luncheon at Mom’s house—working hard and having a good time. Jenner has a fitting this evening in preparation for her forthcoming trip to Paris; tomorrow morning she has therapy at 8, a phone call at 9, and then she has a press junket for The Kardashians’ fifth season right after.
How long will she put up with being filmed for a reality show? She acknowledges, “It’s not my biggest cup of tea.” Furthermore, I’ll be honest—I’ve never felt really at ease while filming. I simply think I’m not very good at it. She’s appreciative of the family time the show fosters, but if it were up to her, her free time would just be spent relaxing at home, whether it meant watching a basketball game with friends or going to bed early with a TV show. Jenner has already discussed the importance of savoring each moment. Though she’s not sure she believes in it, it’s a nice idea none the less.
“To say that not every day is a magical day is really real,” she says. The truth of life is that sometimes all you’re doing is relaxing. Let’s all enjoy it together if it’s a Sunday and you have nothing to do or someone calls. Many individuals believe that life must consist of these monumental events, and social media in particular has made this belief prevalent. individuals often post things like, “All these amazing things are happening to me, and I’m doing it all!” No. I need to constantly remind myself of this. It’s not designed to be a party every day. There are days when you just should relax.
