RIDING HIGH
No activity keeps Jenner quite as present as being on a horse. “In the moment, it’s all I care about,” she says. Balenciaga dress.
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.”
BREAK TIME
Valentino Haute Couture dress.
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.”
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!”
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.”
“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.”
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