Kylie Jenner materialises as if from the ether. It’s impressive. One moment you’re staring out the window, many floors up in a Manhattan skyscraper, your head running with questions – Will she say anything? What will she look like up close? Are people going to be cranky she’s on the cover of Vogue? Is Timothée Chalamet kicking around here somewhere? – the next she is standing right behind me, her bodyguard José hovering a few feet away, the pair having stealthily arrived as smoothly and silently as a pair of Teslas.
“Hey,” she says, upbeat but trepidatious. It is immediately clear she is shy in a way perhaps only the chronically observed might understand. Then, in what transpires as a moment of self-willed bravery for the reality star/beauty mogul/mother/fashion week bombshell/auspice of society’s downfall (pick your poison), she adds: “Can I get a hug?” So we hug, the effect of which is kind of reality-warping, if I’m honest. The matrix unplugged. Pixels made flesh. We are talking about so many pixels here. Using Instagram followings as biography has been problematic, to say nothing of a little naff, since the end of the last decade, but sometimes you can’t fight the numbers: Kylie’s following on the pink app alone is a couple of ticks shy of 400 million. Four hundred million people! Even if a chunk of them are nonhuman, a notable percentage of the world’s population is infatuated (some infuriated, granted) by the daily shenanigans, outfit choices, brand extensions and dispatches from the make-up chair of a 27-year-old Californian, with a sphinxlike approach to fame, who shifts product and inspires opinion on a scale few have experienced. (Elizabeth Taylor? Theodora of Byzantium?)
Kylie is the first of her family to appear on the cover of British Vogue. “I am?” she asks, shocked when I tell her this. “Not Kendall?” She says she cried when she got the call. To the editorial team in London the timing felt like a no-brainer. As mysterious and obsessed over as a star of the silent movie era, Jenner’s cross-border, multigenerational reach has electrified ready-to-wear and couture weeks like no other presence of late.
“I feel like I’m finally finding my fashion feet,” she later tells me. Her usual styling duo, sisters Alexandra and Mackenzie Grandquist, agree: “She has fun with it. She knows herself. [It’s] what makes her relatable to a generation of women.”
Hug over, perhaps the most watched woman of the 21st century thus far takes a seat. We’re in a restaurant near her NYC bolthole that she’s asked I keep under wraps as, by fluke (or more likely those Tesla moves), the press doesn’t always cotton on when she’s in town for meetings or to see her boyfriend. “I’ve been walking the High Line,” she says, proudly. A rare treat. By the sound of it, her life in LA, where she lives with her two children, Stormi, six, and two-year-old Aire, can be a little… compoundy: an airtight lock-up of giga-fame. It’s all about a baseball cap, she explains. “There’s an angle that you can do where they can’t see your face, and I wear a mask.” Though she’s careful not to go full DiCaprio. “He has a distinct incognito look that now is not incognito because people know it so well.” One wonders if, having inspired the prevailing, occasionally chagrin-inducing, aesthetic for young women in the 2020s, a simple face covering makes it easy for her to hide amid her scores of imitators? “I haven’t had one person notice me,” she says, delighted by her East Coast sojourns. “I’ve been really able to get around.” Every cloud…
For now, though, she’s in full Kylie mode. It’s riveting looking at her: like finally seeing the Taj Mahal in person after the ambient consumption of thousands of images of it over the years. Five foot six before the heels, she’s taller and more willowy-seeming in person, wearing a spaghetti-strapped summer dress in white poplin (£110 from July’s drop 007 at Khy, her clothing label) that fits to perfection, some barely-there Kylie Cosmetics make-up (natch), while her hair is full and a little undone, like she’s recently tumbled out of bed, which might be the case, as at one point today our meet-up time was being rolled back by the hour. Who cares now, though. She looks mega. I feel sort of silly even writing this but, defiltered and lit by the relentless sun of a hot Manhattan afternoon, she is strikingly beautiful in a way I’m not sure cameras – or comment sections – do justice.
More curious still is how her eyes pass over a new person. As we chat about the LA-NYC commute and whatnot, it almost feels as if she’s taking an ultrasound of my soul. I’ve never known the like. After a while, some major, taciturn test appears to have been passed when her silvery-brown eye contact becomes unbroken and remains so for the rest of our hours together. It feels rare, unusual and intense, like having tempted a hummingbird onto your fingertips. It is palpable that this is a person who essentially doesn’t trust others. “I learnt at such a young age how to deal with all of this in the best way for me,” she explains of her mash-up of shyness and chaos-inviting level of celebrity. “So I don’t go crazy, if I am being honest.”
Jenner was nine years old when the reality television cameras turned up. This was 2007: Gordon Brown was prime minister, for crying out loud; George W Bush president; war raged in Iraq. It was the last wince of the roaring noughties before financial calamity descended, everyone dressed like an extra in Saltburn (unironically), and Instagram was but a glint in Kevin Systrom’s eye. And Kylie? She orders an Arnold Palmer and says in that soft, familiar So-Cal tone of hers: “I do remember the moment. My mom came into the living room and announced the name of the show. She’s like, ‘Hey, it’s going to be called Keeping up With the Kardashians.’ And I remember Kendall and I were like, ‘Don’t you think that’s a handful?’ She was like, ‘I’m fighting for this because it’s so important that our name is in the title of the show. So that we can never get replaced.’”
Well, that plan worked. The Kardashian-Jenner phenomenon is now a few mascara licks away from its 20th anniversary. For some, the camera-primed, consumer-ready troop is as much a part of humanity’s wallpaper as Coca-Cola or the Euros. Though, of course, the brand they often invoke is Marmite. As the world assesses the triumphs and turmoil of all that the family has come to signify, people are daring to ask: is it actually Kylie – quiet, chilled, resolutely herself – who has become its most riveting member?
And now: haute couture, baby. What larks! The black gown affixed with a faux, hyper-real lion’s head she wore at Schiaparelli in January ’23; frow in a plunging corset top at Haider Ackermann’s Jean Paul Gaultier takeover the same week (also in attendance: one of the world’s most adored young actors, Timothée Chalamet, now her partner); a dip into ready-to-wear for the Prada show in Milan last September in a chic black bodycon dress with crystal skirt overlay, finished with an updo, indoor sunnies and a patent pump; then back to JPG by Simone Rocha this past January, where she sat alongside British comedy It girl Amelia Dimoldenberg, an Aphrodite in sheer ivory with a naked square-toed platform. There’s a lot to be said for letting fashion do the talking.
“I feel like I’ve been in full mommy mode in my early 20s, [so] just to do something more for me after I had my son…” she says, with a smile. “I’ve been way more into the fashion world and fashion week, and it’s been so much fun. I’m like, ‘Why didn’t I do this sooner?’ Every time I go to Paris things just happen. I love the fast pace. It’s a whole new world.”
“One of my first memories with Kylie was a midnight swim in LA, it was the four of us – her laughter, her adventurous spirit and her beauty was infectious,” recalls Ackermann, who is a close friend of the couple. “One could only embrace such a joyful moment, and I knew that we would collaborate on the Met Gala.” Indeed. In May 2023, the designer tooled a custom, crimson and baby blue cutout confection with the Gaultier atelier. The process of its creation was revealing, he remembers. “Her curiosity, her eagerness and willingness to understand, to absorb and to learn is quite impressive, without ever hesitating on her own ideals. She certainly walks her own path.”
The Grandquist sisters concur. “When we prep for a major red carpet, there is a lot that goes into it.” The key? “She knows herself and her body very well.” In essence, the Jenner Jnr fashion explosion is persona meets performance, with each outing planned with a military-grade obsession. “Kylie is a fashion icon because of how she wears the clothing,” say the Grandquists. “She is so involved.”
Yet at every step, Jenner concedes, the scrum of paps that descend on her couture week outings is next level, especially for someone who finds real-world eyes troublesome. “People ask me, ‘How do you deal with all this?’” It’s a few weeks before her 27th birthday, and the unique peculiarity of her setup is on her mind. Kylie sips her drink and looks lost in thought. “I don’t remember a time before,” she says eventually. “I don’t really remember a time before there were the lights and the cameras.”
“She was,” re-emphasises her mother, Kris Jenner, “on Keeping up With the Kardashians from the time she was nine years old.” The family matriarch calls me from Los Angeles a couple of weeks later. Deliciously eloquent and near-comically polite, KJ Snr is 68 going on 30, and the noted catalyst for much of her brood’s success. “I would have the kids film after school or on the weekend. It wasn’t a full-time job, obviously, but it was a place where Kylie felt safe and she was with her family. We made it really fun and she was having a blast. But I think, as she got older, she became something that has such legs, such longevity…”
Kris pauses. “When we started it was a different world that we lived in and we created this fanbase of hundreds of millions of people – if you add up our social media followings it’s billions of people. And you’re having people weigh in and give their opinion. She [had to] protect her soul. She has learnt how to be emotionally available only to the people she feels really comfortable being around. She protects her mental health that way. Anywhere she goes it creates a lot of brouhaha. It can be very overwhelming, by the way.”
For Kylie’s part, she calls her mother her “best friend”. They are wildly close and she is sanguine about her experiences of early fame. “Well, for Kendall and I, we didn’t have a hard schedule or anything. We were in school, so it didn’t really affect our lives. Sometimes we would come home and they’d be filming at dinner. We were never obligated to show up and be on camera.” Yet increasingly, post the frantic blur of tweenage celebrity and 20-year-old motherhood, an existentialism presented itself: “I don’t know who I would’ve been without all these eyes on me,” she says, raking her fingers through her hair ponderously. “I probably would’ve been, like, a different person, I would think.”
“I do think I’m misunderstood,” she continues. By Kylie and Kris’s account, pre-camera Kylie was an all-singing, all-dancing fireball of jazz hands and feather boas, found belting out numbers atop the family pool table, her de facto stage of choice. “Typical Leo,” she deadpans. “Always the loudest and silliest in the room.” But times change. “Now when I walk in a room I’m trying to be quiet. I’m always just…” she trails off.
“Watching?” I posit, as she stares back at me carefully.
“Yeah.”
For all its agenda-shifting, giggle-inducing glee, can we all agree at this point that social media shares certain qualities with a hellscape? I’m not sure anyone feels it more keenly than the fifth most followed account on Instagram. Increasingly, Jenner is trying to allow headspace for the unique predicament she found herself in as a teen. “That was 10 years ago now. Naturally you’re in such a different place,” she says. Yes, there have been cosmetic procedures – with hindsight, she now wonders if she might not have had a boob job so young – but the judgement levels, my God. “The world put a lot of pressure on a teenager, me, to make the right decisions. And I just have to be gentle with myself because although I carried so much responsibility in the moment, I was just trying to do what was best for me. I was just trying my best as a human. I have to realise: ‘It’s OK, Kylie.’” She still sounds shocked by it all, truthfully. “Looking back, I’m like, ‘God, I was 17, 18.’”
Jenner still lives in the ego-tumbling scenario of being both villain and victim-in-chief of the internet’s obsession with personal aesthetics. An undignified alliance of Facebook mums, fashion snobs, brutal teens and Russian bots continue to track and comment on her every thong shot. There is an army of KJ stans too but, lately, she’s been reassessing her relationship to the mess of it all. It’s no coincidence that this has come as Stormi reaches the age she’s aware of all a smartphone can do. “I have this daughter and I just want the best for her and I want her to just love herself unconditionally,” says Jenner of her evolving relationship with herself (personal and virtual). “It’s taught me so much.”
“It’s like the whole mom thing, really,” she goes on. Remind me how old you were when you had your first? “I was 19 when I got pregnant, 20 when I had her.” Wild, I say before catching myself. But Jenner gets it. “I know,” she replies, her eyes warm with humour and wisdom. “It was wild.” She adds, “Looking back at it, I give myself more empathy and grace. But when I was a teenager, even my family were like: ‘You aren’t that young.’ I think maybe I carried myself [a certain way] or I’d already been working for 10 years. It didn’t hit me [straight away]. But it was a huge life change.”
She suffered from prolonged postpartum depression after both of her children’s births. “Stormi’s lasted a year,” she says, Aire’s around the same length of time. “I’m going to be 27, and I’m finally feeling like myself again, and [looking back] I think, being pregnant, I wore sweatpants every day, I didn’t have time to figure out even some of the little things in my life, and then postpartum lasted a year. Mentally, it’s really hard. Hormonally, it’s really hard. I didn’t know how to dress,” she says, smiling, still distressed by it all.
“It hit me differently both times. Probably with my son it was major baby blues, so I was just so emotional over things that I probably wouldn’t be that emotional about [typically]. On the phone with my mom all day hysterically crying, saying, ‘I can’t figure out his name.’ Now my advice to all my friends having children is pick the name before, because when the hormones hit you can’t make decisions. You can’t,” she cries. “When I met him, he was just the most beautiful thing to me and I couldn’t believe just how perfect he was. I felt like such a failure that I couldn’t name him. He deserved so much more than that. It just really triggered me.”
It took her a year to settle on Aire. “My son’s name was actually Knight for a long time and my daughter, still to this day, is like, ‘Do you remember when Aire’s name was Knight?’ And I’m like,” here Jenner slips into the ultimate mum tone: “‘No.’ And she’s like, ‘That was so funny, Mom. I like Knight better.’ And I’m like: ‘You know what, we are not doing this again.’”
She rolls her eyes contentedly. Motherhood is “everything” to her. “Stormi wasn’t planned. It happened, but obviously I knew that I wanted to have her. I wanted children so bad.” Her boyfriend back then, megastar rapper Travis Scott, is father to both Stormi and Aire. Her decision to become a young mother – despite the reams of judgy commentary it incited – makes sense when you consider the particulars of life. “No matter what I’m going through or what I look like or what the internet writes about me that day,” she says, her chill momentarily punctuated by passion, “I come home and my kids just love me unconditionally. They’re just obsessed with me and that’s taught me to walk through life a little easier. I’m like, ‘OK, well I have these little humans at home that need me and love me and think I’m the most perfect person in the world, so I don’t really need validation from outside sources.’” Amen.
It’s been a road, though. “The tricky part is figuring out the balance of growing up with your kids. I have to remind my friends who don’t have kids all the time, who are like: ‘Let’s do this in the morning!’, that I have children. Letting go of your selfishness and your freedom at a very young age…” She exhales. “I don’t think we realise how selfish we are as human beings until we have children. But, you know, that is also the biggest pro.”
She could have done without the relentless public body shaming. Go figure. “I was 200 pounds when I gave birth to my 9 pound babies: 8.3 and 8.9,” she says. “I finally lost all the baby weight after my daughter and then got pregnant with my son two months later.” She and Travis had been on a break, essentially split up, but rekindled things when they lockdowned together with Stormi during the pandemic. “And I felt in shape and it was working out, and then I got pregnant and did it all over again. I feel like people didn’t give me, or give women in general, enough empathy. I see pictures [online] and people are accusing me of being on drugs or something…” You mean they mistakenly think you were taking Ozempic, or some such? “Yeah.” She’s annoyed by it, pointing out people forget she’s just a 20-something post-kids. “I’m back at my weight I was before I had my daughter and son and people are putting side by sides of me three months postpartum. I’m like: ‘Does everyone forget that I had two children and I gained 60 pounds both pregnancies?’”
Later, I Zoom with one of the few friends to go the distance in Kylie’s inner circle: Anastasia Karanikolaou, internet sensation, all-round LA hottie and charisma machine. Stassie, as she is known to her millions of followers, met Jenner at an LA bookstore when they were 13. Karanikolaou recalls Jenner was wearing some sort of Halloween costume – “Even though it absolutely was not Halloween. I thought: ‘This goof is as crazy as me.’” They had a sleepover that night. Their lives have been intertwined ever since.
She says people never see how truly “silly” Kylie is. “We used to make videos on this pre-Vine app together when we were teenagers and people were honestly like, ‘Are you two on drugs?’ because we were so incredibly weird,” she says, laughing. Yet at the same time: “I know I can call her crying and she will sit and talk me off the ledge.”
When Karanikolaou’s mother passed away last year, Jenner dropped everything. “Kylie sat on the couch with me for four days, sometimes in silence, sometimes talking or watching TV, whatever I needed. She is such a ride or die,” she says. “And she is an incredible mother too.”
Everyone I speak to mentions Jenner’s “soul”. It seems possible the deadening grip of perma-scrolling may have given the world the wrong idea about her. She’s a dreamer too. I keep thinking of that pre-fame little girl. Did you actually kinda want to be an actor or a popstar before social media came for you? “I think so, yeah. I always knew I never had a fantastic voice or anything…”
I beg to differ, I tease. I saw you singing the alphabet to Aire on an Insta Reel the other week. “I should be a singer,” she says, brightening, kind of joking then suddenly not. “Maybe in another lifetime. No, seriously. Maybe when I am done making clothes, I’ll get into the recording studio.” She has flipped into manifesting at this point, pulling up her current playlist on her iPhone to show me it is wall-to-wall classics – Aretha Franklin, The Beatles, Otis Redding – with the occasional modern banger tossed in. “‘Please Please Please’ is the best,” she says, scrolling past Sabrina Carpenter’s summer smash. (I’m guessing the lyric “I heard that you’re an actor, so act like a stand-up guy” has a unique piquancy for her.)
For now she is busy finding her daily life mind-boggling. “I’m 26 and I have a first-grader. I’m going to be 40 with a 20-year-old,” she cries, then adds: “And we’re going to be best friends.” What’s the school sitch like: carpooling, group chats, the whole parenting shebang? “We have all of that.” How are the other mums with you? Is it all, “Oh, my God, it’s Kylie Jenner…” Forget fame: age gap is the kicker, she says. “I always just feel like the young mom in the room,” she says, in a way that suggests she hasn’t quite worked out her place in the wider parenting ecosystem. “No one obviously makes me feel any type of way,” she adds of the other mums. “I’m just like,” and here she slips into a pretend, cute little voice: “‘Here I am.’” She’s happy that coparenting is going well, though. “If I’m away, for example, if I’m here, they’re with their father,” she says of the children, who split their time between California and their father’s place in Texas. She tools her entire schedule around them and on the “very rare” occasions she and Travis are both travelling, they stay with her sister, Khloé, whose daughter, True, is in Stormi’s class at school.
As for love, she doesn’t like talking about Timmy. “Privacy is so important to me in life,” she says – a response that might cause a fair deal of head scratching for some. Yet does it also make perfect sense? Perhaps, I ask, you haven’t been blessed with a great deal of privacy in your life sometimes? She nods, ever thoughtful. “Yeah.” Then she smiles. “It feels so good.”
It is noted that Chalamet managed to do two global press tours recently – for Wonka and Dune: Part Two – without being asked to sit and dish on the relationship, so why should she? I wonder if that’s down to sexism or another sort of power dynamic to do with tiers of celebrity – probably a bit of both. But they’re together, and occasionally out and about: Beyoncé concerts, the US Open, the Golden Globes. A lingering snootiness exists in some corners, especially online, that she is a mismatch for an Oscar-nominated movie star. Having met them both, I would say he is also playful, emotional and kind, and not immune to the charms of extremely beautiful and successful women. I’d warrant the gentleman in him would leap at the chance to point out that he’s the one punching.
With an individual net worth high in the hundreds of millions, Kylie is, famously, a very wealthy woman. It’s been reported that her real estate portfolio alone is worth an estimated $80 million. But don’t let the yacht selfies entirely fool you. The hours are still intense. She has her Sprinter vodka seltzer brand (surprisingly delicious), and heads up the institution Kylie Cosmetics, of course. Then there is her clothing label Khy, launched last year, which sells the distilled essence of that easy, clean, sexually confident, body-conscious, occasionally whimsical KJ look via a series of drops online and in pop-up stores, some of which she collaborates on with interesting young designers, such as London-based Natasha Zinko and Berlin-based clubwear brand Namilia.
Design development, product testing, marketing, legal, thousands of emails, hundreds of photoshoots, mostly involving herself, to say nothing of her commitments to shooting the rebooted The Kardashians on Disney+, two kids, a love life and – you know – being 27 (“I am young, don’t forget!”), it adds up. Though it’s clear where her heart lies for now: “There is nothing more fun in this world than cosmetics and fashion. The Lip Kits have been around for so long,” she says of the legendary beauty product that started it all for her. “Ten years now, so fashion is my new baby and I am having the most fun. But they go hand in hand.” She smiles, absentmindedly shaking out her hair again, backlit by the sun, a perfect visualisation of all she proliferates. “Every fashion look I wear has so much to do with the glam.”
Five days later we are in Paris, where the glam is certainly glamming. In the quietude of the Hôtel Salomon de Rothschild’s basement ballroom, carpeted for the occasion of the autumn 2024 Schiaparelli Couture show in thick, black shag pile, its towering walls swatched in panels of inkiest velvet, it feels rather like waiting inside an empty jewellery box for the gems to show up. And show up they do, later in artistic director Daniel Roseberry’s well-considered collection, but firstly in the curtain-raising form of Kylie – jetting into Paris for less than 24 hours – who glides into the room in a snowstorm of camera flashes in a crystal-embellished couture gown, her head entirely veiled in a wrap of lightest peach.
I’m unsure whether this speaks more to her kindness or madcap sense of fun, but she’d asked the nice folks at Schiaparelli if we could sit together to watch the show as she doesn’t really know anyone else attending and fancied a chitchat. Alas her powerhouse presence requires a whole other level of choreography. No sooner has she entered the building than her arrival video begins clocking up 11 million views on British Vogue’s Instagram alone, while the keyword “veil” starts trending on Google. Instead, show over, I bolt across from the other side of the runway and dive head first into the day-to-day indignities of fame, as her no-smiles security team whisk us through the thronging, staring crowd, out of the luxurious salon, through a hidden swing door, where, secret service style, we are reunited by the room service lift under some especially stark lighting.
“Giles!” she exclaims sweetly and air kisses me as warmly as one can with a head fully encased in cloth. We take the lift up to ground level and wait at the side of the hotel’s walled gardens. Then, suddenly, it’s go, go, go, darting through the crowds, past the paps – “Kyliee! Kylieeee!” – and into a people carrier so blacked out it is as if a perpetual twilight has descended, bound for The Ritz.
Job done, adrenaline pumping, crammed in with today’s beauty squad (Ariel Tejada, make-up; Jesus Guerrero, hair), Jenner is in her element. Within minutes the veil is off… in every sense. This vibe is taking my circadian rhythm to 4am, I say, taking in the car’s club lighting. “It’s taking us to the party,” whoops Jesus. “Are we Vegas-ing, what’s happening?” Kylie says, laughing. “Should we take a shot?”
It is often noted – sometimes ungraciously – that Jenner’s nerves are visible when she’s out in public. “We always say,” she sighs, “the second we land somewhere: ‘All right, it’s time to be Kylie Jenner, I guess.’” To manage her fears, she goes into character mode. “Keeley Jenner is what they call me,” she says, pointing at Ariel and Jesus. “We don’t know how that’s spelled,” confirms Ariel. “It happens when we’re delusional.” “When we’re exhausted,” says Jesus. “They even have a song for me,” says Kylie, proceeding to sing, to the tune of Roy Orbison’s “Oh, Pretty Woman”: “Keely Jenner walking down the street, Keeley Jenner, the kind I’d like to meet…”
It’s all getting rather giddy, just the way she likes it. Soon, she is telling me about a girl who came up to her the previous evening asking for advice. “We had this fan, she was the cutest, who said: ‘Do you have any wise words to say to a 20-year-old?’” At this, Jenner does a comedy eyeroll. “Well, first of all, I’m only 26, but whatever…” So what did you say? “I was totally on the spot and everyone had their phones out and I didn’t know what to say,” she recalls, panicked. “So I just said… ‘Don’t listen to the haters.’” At this, she does a full body cringe as Ariel and Jesus fall about laughing. “That girl wanted wisdom and I came up with that…” she gasps, appalled. “God, I need to get on that plane so I can sleep.”
Soon we are tunnelling beneath the Ritz where she will do a quick suite-stop and de-couture before heading to the airport. Her empire awaits. Her children. Her life. The business of being Kylie. As we exit the people carrier, her crystals sparkling under the strip lights, right on cue someone from across the echoing parking lot shouts, “I love you!” Without missing a beat, eyes twinkling at the ridiculousness of life, at herself, at the world at large, Jenner gives me a knowing look and yells back over her shoulder: “Don’t listen to the haters!”
