Entertainment

How Kylie Jenner Succeeded in DL Dating, Family, and Fashion: “I’m Having The Most Fun”

Kylie Jenner is as polarising as she is influential. Yet, despite hundreds of millions of eyes following her every move, the life, loves and longings of the woman herself have remained shrouded in mystery… until now. For the first time, from Paris couture, via New York and LA, she lets British Vogue into her world. By Giles Hattersley. Photographs by Luis Alberto Rodriguez. Styling by Ib Kamara

​​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 nɑƙeɗ 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.”

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