20/20 VISION

Glasses, Prada. Bag; necklace; sandal, Miu Miu OPPOSITE: Bag; sandal, Prada

Portrait of Tammy Strobel
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Sunglasses; Book Tote; necklace; earring; bag; sandal, Dior OPPOSITE: Ring; bags; shoe, Fendi
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Photographed by Don Penny. Styled by Judith Trezza


With a billion-dollar makeup-and-skincare business, Kylie Jenner is having her cake and eating it too.
My Reading Room

"Dress, Dolce&Gabbana Alta Moda Opera. Hat, Christine A. Moore Millinery. Earring; necklace, Bvlgari. Vintage ring, Beladora"

The offices of Kylie Cosmetics occupy the top floor of a boxy steel-and-glass building near the freeway in Calabasas, just outside Los Angeles, down the road from a shopping centre, a cluster of fast-food restaurants and a budget motor inn. If you were blindfolded and deposited in front of the building, and asked to guess where you were, you might say Utah. Gusts of cool December wind blow dead leaves and dust. Towards the end of my hour-long drive up from LA, an actual tumbleweed rolled along the shoulder of the 101.

Kylie Jenner—22-year-old beauty mogul, mother of two-year-old daughter Stormi Webster (with her ex, rapper Travis Scott), and youngest member of the Kardashian-Jenner clan—is somewhere inside that building, in the midst of her transformation into Marie Antoinette for Harper’s BAZAAR.

Long-time fans of Keeping Up with the Kardashians (or KUWTK) remember Kylie as the precocious tween on the series, which debuted in 2007, when she was just 10. Early on, Kylie and her older sister Kendall—matriarch Kris Jenner’s children with her then-husband, Olympic gold medal winner Bruce (now Caitlyn) Jenner—would get into sitcom-style high jinks that provided a wholesome counterpoint to the more grown-up drama that embroiled older Kardashian siblings Kourtney, Kim, Khloé and Rob.

But over the past five years, the Jenner sisters have forged their own paths: Kendall, as one of the top models in fashion and Kylie, as the mastermind of a beauty brand that started out selling pout-enhancing Lip Kits and now includes a full suite of makeup and skincare products, with more on the way. Kylie and Kris, who run the business together, recently sold a US$600 million majority stake in the company to beauty conglomerate Coty, which puts the valuation of Kylie Cosmetics at more than US$1 billion.

Back to the Kylie Cosmetics offices: The first clue that you’re in the presence of a member of America’s best-known family is the sizable security guard just inside the glass door at the entrance. There are three more like him when I step off the elevator at the Kylie Cosmetics floor, all ready with stickers to cover the camera on my phone. The walls are painted white, with black and soft pink accents, and the floors are polished concrete. Along one wall, a console is stacked with magazines featuring various assortments of Kardashians and Jenners on the covers: Kim and Kanye; Kylie and Kendall; Kim, Kendall, Kourtney, and Khloé solo; Kylie and Kris; and a few with all of them together—the whole Kit and Kaboodle.

In another large room, which has been turned into an impromptu photo studio, there is a champagne vending machine. Over the course of the shoot, two people wander over and try to buy a split of bubbly, but neither of them can figure out how to use it or if it even works. In the kitchen, there are glass-door fridges filled with water, juice, Pedialyte and Mexican Coke. On the counter is a jar of Oreos stacked in the precise way that Kylie’s sister Khloé is known to prefer. Others are filled with pink candy. Throughout the office, there are baby pink velvet ropes on baby pink metal stands that exist, it seems, to keep camera crews—a near constant presence—away from the areas where Kylie’s employees actually work.

Roughly 20 people in neat cubicles and glass-walled offices, all armed with identical baby pink staplers and tape dispensers, keep the business of Lip Kits, Kyshadows and Kylie Skin, the newly launched skincare brand, running. They’re surrounded by some 1.2m-tall pictures of Kylie in an array of provocative poses. Her famous pout—the one that has sold thousands of Lip Kits—is the focal point. That is, if you can take your eyes off her body. When I first spot Kylie, she’s wearing clipped-in hair extensions and a white dress. But then she disappears for about an hour and returns, styled in a high powdered wig and Dolce&Gabbana couture, as the last queen of France. Fittingly, she’s trailed by a gang of four people—an assistant, a hairstylist and his assistant, and a makeup artist with boy-band facial hair. They travel in a pack, just steps behind her, like courtiers. At one point, one of them leans against a plastic Doric column, made to look like marble, that was brought in for the shoot. It crashes loudly to the ground.

You may be wondering why you’re this far into a story about Kylie Jenner and you haven’t heard much from the subject. The interview has been scheduled to begin once the shoot is done. But after 10 hours of high-concept hair and makeup, and multiple wardrobe changes, she has little more than a half hour to talk. It’s 7pm and Stormi’s bedtime is approaching. Kylie wants to go home.

I ask her if she ever envisioned the kind of success that she’s enjoying with Kylie Cosmetics. “I didn’t think it was possible,” she says, wrapped in a fluffy pink robe as she gets her makeup and wig removed while her entourage waits nearby for it to all be over. “I didn’t think that this could really be my job. I always loved makeup though. I wanted to watch tutorials. I would play with my own makeup or my mum’s. I’ve always loved makeup and I was obsessed with lipstick.”

“Kylie does all of the creative stuff—she’s the CEO, CMO, CCO,” Kris Jenner tells me later. “She’s been so amazing, the way she has grown this company. I’m like the COO. I help keep everything running behind the scenes. But she had this vision when she was 15, and it’s been remarkable to watch it come to life, to step back and see it evolve.”

The Coty partnership, Kylie explains, will allow her to focus on creative and communications efforts for the brand as she, Kris and Coty look for opportunities to grow internationally. “I think it was just time,” Kylie says of the Coty deal. “I mean, we have a great team. But it’s me and my mum kind of leading the pack, which will still be the case. Nothing’s going to change. But hopefully, we can expand and get a big infrastructure behind Kylie Cosmetics, and go worldwide and get more amazing people on the team to expand the business.”

Unlike their siblings, Kylie and Kendall grew up for the most part in the glare of reality TV. Kylie says she doesn’t remember much from her family’s life before KUWTK. “Even before the show, my dad always had an audience, so I was always around that energy,” she says. “I don’t know. I think it’s a blessing, the way it happened so early, because I don’t really know what it would be like to not be famous or in the limelight.”

“My dad was the one everyone knew when we were little,” says Kendall. “We would just get excited because people would invite him to bring us to Disney premieres. I mean, that was the highlight! But the show wasn’t a big deal to us when we were really young. It was just our normal. We also got to grow up with a bunch of older siblings, who were mostly adults, really. I posted a picture recently of Khloé giving Kylie a bath in the kitchen sink when she was little, and that’s what it was like. We had, like, 75 parents. We learned from them, from their mistakes.”

My Reading Room

Ballgown, Giambattista Valli Haute Couture. Earrings, Buccellati 

My Reading Room

Gown, Oscar de la Renta. Headpiece, J.R. Malpere. Earrings; cuff, Buccellati. Shoes, Roger Vivier OPPOSITE: Dress, Carolina Herrera. Headband, Piers Atkinson. Earring; bracelets, Beladora. (On Stormi) Dress, Susanne Lively Designs. Bonnet, Adeline & Frankie by Baby Beau & Belle. Socks, Bonpoint. Shoes, Baby Beau & Belle. Bracelet, her own 

My Reading Room

Kylie lives in the Oaks, a double-gated community, just “35 seconds away” from Kris and other members of the clan. Until about 10 years ago, Calabasas was considered a sleepy suburb of LA; now, it’s among the most searched neighbourhoods on real estate site Zillow. I say this only to demonstrate how adept the Kardashian-Jenner brood is at making things look glamorous. In a few short years, Kylie—under Kris’s watchful eye—has built a billion-dollar business and amassed an army of 157 million (and counting) Instagram followers by making everything and everyone around her appear irresistible to her fans.

It’s a bit of a wonder that Kylie has agreed to answer questions at all. Social media has afforded her a direct line of communication with the world. She controls her own domain, and shares only what she wants to and not really that much more. As further proof of Kylie’s influence, her first photo of Stormi, posted on 6 February 2018, was the most liked image ever on Instagram for nearly a year; it was supplanted by a picture of an egg. (As of this writing, she still has three of the top 10 most-liked posts of all time on the platform and seven of the top 20.) In 2018, after Kylie tweeted her disappointment in Snapchat’s redesign, the company’s stock lost US$1.3 billion of its value.

I ask Kylie when she first became aware of the power she wielded. “Probably more when I was on the red carpet with Kim,” she says. “I always knew my family was a big deal, but me, solo, probably around when my pop-ups started. Or when I started dyeing my hair blue and cut my hair off, and then everyone started dyeing their hair blue and cutting it off. And I was like, ‘Whoa.’ I realised what an influence I had. I was probably like 16.”

Of all the Kardashian-Jenners, it’s Kylie who most seems to share Kris’s entrepreneurial impulses. “My siblings compare us all the time,” Kylie says. “I see my mum almost every day; I was over there last night. I’ll just go by her house. We’re always here working together, doing different things, or taking meetings together. But I actually think we all have a lot in common. I feel like I can relate to every single one of my family members in a different way. I think my mum and I are very similar, but Kourtney and I also have similarities. Kendall and I are very adventurous and athletic. Khloé and I are free-spirited and silly, and Rob’s very silly.”

Kylie theorises that her mum had her children in sets of two deliberately. “Everyone has their own partner,” she says. “Kourtney has Kim. Khloé has Rob. Kendall and I are so close in age. We have a close bond, but we’re definitely polar opposites. But it works out. We don’t ever cross. She does her thing and I do mine, then we come together and have a great time.” Kendall agrees: “She likes black; I like white. My room was white and silver and gold, and hers was black, really dark. Kylie had a zebra pattern and I had leopard. We responded to each other, so we would have our own thing. But we have similarities too; we’re definitely sisters.”

Kendall says that when they were kids, Kylie was the outgoing one. “Kylie loved attention,” she recalls. “She was obsessed with the Shakira song ‘Hips Don’t Lie’, and she’d go up and put on a belly dancer outfit and come back and perform for everyone. It was like, ‘Hey! Everybody watch Kylie... again!’ ”

The five years since her father publicly came out as a trans woman have been rocky ones for Kris and her ex-husband. But Kylie says she remains close to Caitlyn. “My dad was the best growing up,” she says. “Never missed a sports game. Took us to school every day, and our school was like 45 minutes from our house.” I ask Kylie how often she speaks to Caitlyn. “Like, every day,” she says. “Except I couldn’t talk to her for three or four weeks when she did that show I’m a Celebrity... Get Me Out of Here! (the British reality series in which Caitlyn appeared as a contestant last year). I watched clips online. It was hard to be out of touch for that long, but I feel like it was harder for her because she couldn’t see us.”

During the shoot, Kylie enjoyed a brief visit from Stormi, who seems as happy and delightful as she does in Kylie’s Instagram Stories and YouTube videos, and on TV. Though Kylie and Travis Scott are no longer together, she says she’s determined to make sure their daughter has the same kind of two-parent support she had. “We have such a great relationship,” Kylie says of Scott. “We’re like best friends. We both love Stormi and want what’s best for her. We stay connected and coordinated. I think about [my parents] in situations with Stormi, what they would do. They were very hands-on with me and I want the same for Stormi.”

One thing lifelong fame has prepared Kylie for is coaching her daughter through the experience of being such an object of fascination. “I think about it a lot because the world is just so crazy now,” she says. “Exposing her to all of the negativity that comes with the internet, I think about that too. I’m just trying my best, even though she’s still little, to remind her how blessed we are and that this isn’t normal, the way we live. It’s just our life. People want to take pictures. I think she’d feel differently if I was always covering her face, like, ‘Don’t look!’ ” Does Kylie see more kids in her future? “My friends all pressure me about it,” she says. “They love Stormi. I definitely feel pressure to give her a sibling, but there’s no plan.”

Away from work, Kylie says she has become more of a homebody. “After I got pregnant, I spent so much time at home; I love it,” she says. “I love to lie in my bed and watch movies and forget about the world. Sometimes, I take some time off, let the nannies take days off, and hang out at home with Stormi.” I ask Kylie if she has ever attended Kanye’s Sunday Service. “I have and it’s amazing,” she says. “The reason I don’t go more often is that it starts at 9am on a Sunday and if I’m not working, that’s not a time I like to be out.”

As the elaborate makeup comes off, Kylie’s face is slowly revealed. The freckles she had as a kid are still there. Her eyebrows are surprisingly regular. She’s pretty without the contouring and the drawn-on lips, like she could put on jeans and a sweater, and go grocery shopping unnoticed.

“I think it’s a rare situation when your entire family is in the same position as you,” Kylie says. “I think that has a lot to do with why we are still us. We all keep one another grounded. Kim or Khloé or Kendall can’t just start acting different one day. We all keep one another in check and support one another. I have their support, and I can always run to my mum or my dad or my sisters, and they all know what we’re going through.”

One thing the Kardashian-Jenners are is a united front, and when Kylie says they don’t compete with one another—or anyone— you kind of have to believe her. “I mean, who would we compete with?” she asks, cracking a smile. Her friends, like a queen’s loyal court, giggle on cue. “We have such a life,” Kylie says. “I swear I’m like, ‘We should have a TV show.’ ” 
My Reading Room

Swimsuit; sandals, Tom Ford. Hair clip, Mignonne Gavigan

Makeup: Ariel Tejada using Kylie Cosmetics Hair: Jesus Guerrero Manicure: Chaun Peth using OPI Production: Folabi Quadri /Quadri Group Set design: Natalie Fält Set decor: Annika Fischer 

Photographed by Morelli Brothers.
Styled by Joanna Hillman