Kylie Jenner has decided to go topless. “I want to try something new,” she says, eight hours into her photo shoot on a balmy Monday evening in L.A. Jenner is wearing round nipple pasties, a pair of pink, latex evening gloves and matching high-waisted panties that barely cover her butt. In front of her is a full-length mirror strategically stationed so she can perfect her angles. Jenner is constantly watched by millions of people on Instagram, Snapchat, reality TV, and every other media platform you can name—and right now she can’t help but watch herself either.
There is, however, one condition attached to her decision: some privacy. All the men have been booted out of Jenner’s room, save for her boyfriend, Tyga (“T” to her), who lingers in the back. “I’m comfortable with my body, but not that comfortable,” she says. “I’m not going to be walking around like that with a bunch of guys there.”
The women allowed to stay—mostly Jenner’s personal entourage, made up of stylists, makeup artists, hair stylists, assistants, etc.—mob around her as she poses for photos. She leans on her right leg, cups her breasts, and whips her lofty ponytail back and forth. “Yassss, Kylie!” someone screams.
At 19, Jenner has seemingly spent more of her life on camera than off. The youngest daughter of Caitlyn (born Bruce) and Kris Jenner, she first starred alongside her family—that’s Kendall, Khloé, Kourtney, Kim, and Rob—on Keeping Up With the Kardashians, the hit reality TV show now in its 12th season, when she was nine. Since then, she has become a magnet for tabloids and paparazzi, as well as teens and millennials who want to be just like her. At press time, Jenner had 71.7 million followers on Instagram and 17.6 million on Twitter. In 2014, she was named one of the most influential teens by TIME, and dubbed the most famous Kardashian by outlets like Us Weekly, Bloomberg, and Business Insider.
“When I was younger, I used to think about my sister’s name, Kim,” Jenner says. “Growing up with her, I always knew her name, but now everybody else knows it, too. That’s so crazy! It feels different when you say it now: Kim Kardashian.” She emphasizes each syllable of her sister’s name to convey just how inconceivable her fame is. “Now, I feel like that when I say my name. Kylie Jenner. Fuck! Everyone knows my name too.”
But unlike Kim, whose initial claims to fame were a sex tape and reality TV, Kylie is a new kind of celebrity: one whose stardom is fueled primarily by the image she portrays on social media. That fame—along with the Kardashian-Jenner name, of course—has opened many doors for her. She has collaborated with Sinful Colors on a nail polish collection, and is the owner of a successful cosmetics line, Kylie Cosmetics, which produces her wildly popular Lip Kits and other products. She and her sister Kendall, 20, have designed a line for clothing brand PacSun; launched their own apparel and accessories label, Kendall + Kylie (sold at Neiman Marcus, Nordstrom, and Saks Fifth Avenue); and partnered with app publisher Glu on their own mobile game. Kylie also created a self-titled paid app, which offers her fans exclusive access into her life via videos, behinds-the-scenes pics, and more; it’s one of the 10 top-grossing entertainment apps in the U.S. In February, she became the latest face of Puma. She’s only in her teens and has already built her own empire.
Jenner is aware that fame has afforded her opportunities that most teenagers can only dream of. “It’s definitely easier for me than for most people,” she says. “There are so many doors that I’ve walked through.”
But she also struggles with the trade-offs. Jenner says she has been cyber-bullied since she was in her early teens and criticized for her body. Her romantic relationships are fodder for tabloids. “I don’t hate my life,” she says. “I’m happy. But everything that comes with it—the paparazzi and not being able to do normal things? I’ve been famous for what feels like my whole life. I just want to know what it feels like not to be.”
Spending time with Jenner, it’s clear that sometimes she’d just like to be a normal teenager. But it’s equally clear that’s simply not possible.
The day before the photo shoot, I meet Jenner at Chateau Marmont, the legendary Sunset Boulevard hotel that has housed some of Hollywood’s wildest parties and trysts. In person, Jenner looks much shorter, but just as alluring. She’s just finished lunch with Tyga and is wearing a white skintight dress, silver metallic booties, and a silver satin bomber jacket. The Chateau is one of Jenner’s regular destinations, perhaps because it’s among the few places she can go and be left alone. Sitting on a hill overlooking West Hollywood, it resembles a white castle, with secret entrances and exits perfect for Hollywood stars. The staff is famous for its discretion. An exclusive celebrity hideout isn’t a regular environment for most 19-year-olds, but Jenner can’t exactly go to the Grove unnoticed.
“I still try to do everything that I really want to, like go to the mall,” she says in her gentle voice. “But once I get there it’s not a fun experience anymore.”
Jenner has built her fame on sharing her life on Instagram and Snapchat, but she’s also careful to keep big parts of it secret. “I don’t sit around and stare at my cars and Snapchat them,” she says. “That’s what people think I do, but there’s a big part of my life that I don’t like to show. I’m ‘Kylie Jenner’ to the world, but I’m just ‘Kylie’ to my friends and family.”
For example, Khloé remembers her sister’s goth phase during the sixth grade, when Jenner had black hair with a blonde stripe and bangs that hid her eyes. Her uniform often consisted of red-and-black fishnets and the blackest eyeliner she could find. “We were like, ‘What is going on? Kylie, you can’t dress like this!’ But she just did not care,” says Khloé. “Most 12-year-olds would probably cry and change. She was like, ‘No! I’ll stop when I’m ready.’ Nothing can sway Kylie. She’ll do what she wants to do no matter what.”
But Jenner only shows small glimpses of “Kylie” to the public. “I already give so much of my life,” she says.
In a Keeping Up With the Kardashians episode this past June titled “Fake It ’Til You Make It,” Kylie, Kendall, and Khloé disguise themselves with prosthetics in order to experience a “regular” day as “regular” people. They take a Hollywood celebrity tour but their cover is blown by paparazzi. “It was really fun, but I don’t think we got to fully live it out,” Jenner says. “I wish we got to go to Six Flags or somewhere really public and see what that was like.”
Jenner is quick to note that “fame isn’t bad,” but growing up in the spotlight is challenging. “It’s probably the hardest thing,” she says. “You don’t know who you are. I didn’t know who I was a year ago, and I still don’t know exactly who I am now. You’re trying to grow up and make mistakes and everybody’s watching.”
When Jenner was in her mid-teens, she shared parts of her life on Keek, a free online social networking service that allows users to share short videos. “My Keek days were wild,” she says. “I showed everyone my funny and crazy side.” Her clips included filming make-believe fight scenes, making silly faces and voices at the camera, and singing, karaoke-style, Kanye West’s “Blood on the Leaves” in a public bathroom. “That’s when people started making fun of me,” she says. Mean comments on Keek and online made her insecure, and more closed off. “When people bully you about what you want to do, or for being silly and funny, it makes you not want to be silly and funny anymore. I started to lose a lot of myself, pieces about myself that I liked the most.”
In 2014, Jenner faced one of her most acute controversies when rumors began circulating that she had received lip injections. Jenner was pressed about the topic in nearly every interview. At first, she denied the rumors and insisted her lips looked plumper because of makeup. Then, in a 2015 episode of KUWTK, she finally copped to getting filler injections when she was 16.
“It has been an insecurity of mine all my life,” she says now. It all started when she was in middle school. “This guy I kissed was like, ‘Your lips are really small but you’re a really good kisser. I didn’t think you were gonna be good at kissing,’” she remembers, crossing her arms and hunching over. The conversation obviously makes her uncomfortable. “It was so rude. From then on, I just felt like I saw guys staring at my lips. I felt like no one wanted to kiss me.”
She lied about the fillers because, at the time, she thought it was the right thing to do. “I wasn’t even 17 yet,” she says. “What if I came out and said, ‘Oh, yeah, I got my lips done’? What are all those moms going to think about me? These kids, my fans, they’re going to think I’m crazy. I didn’t want to be a bad influence. I didn’t want people to think you had to get your lips done to feel good about yourself. But they thought it was crazier that I was lying about it because it was so obvious. I wish I had just been honest and upfront.”
Jenner admits that she got carried away with the injections. “When you first get them done, you’re like, ‘Oh, it could be a little bit bigger on that side.’ I’d go back and be like, ‘They went down’ and think they could be bigger. But I went too far. It was very painful.”
Jenner still gets the injections but says she doesn’t go overboard anymore, noting that she never had permanent plastic surgery. “It’s annoying to hear every day that you’re just this fake, plastic person when you’re not. Every single day there was a news story about me.”
The social media frenzy came to a head in April 2015, when the #KylieJennerChallenge, a viral sensation that had teens placing drinking glasses over their mouths and sucking in to plump their lips like Jenner, flooded the internet. It was tough to handle. “I used to have a lot of anxiety. I never went out. If I tried to go to the movies or something, I would stop breathing in the middle and just cry. I’m surprised there aren’t videos of me out there. I felt super trapped, like everybody was watching me. I felt like everyone was hating on me.”
Jenner credits her mother, Kris, for helping her find ways to overcome her anxiety. “I learned to slow down everything, focus on things that I love, and say no to things I didn’t want to do,” she says. “I used to [agree] to do everything, but when I started taking control of my life again, I felt better.” In December 2015, she got the phonetic pronunciation of the word “sanity” tattooed in red ink on her right hip to remind herself about the importance of maintaining stability in spite of her celebrity.
“At the end of the day I have to live with everything I do,” she says. “I’m just proud of myself for not going crazy. Tyga helped me with that a lot.”
In late 2014, rumors circulated that Tyga, who had recently called off his engagement to model Blac Chyna—now engaged to and expecting a child with Rob Kardashian—was dating Jenner. At the time, Tyga was 25 and Jenner was 17. Sex between an adult and a minor in the state of California is illegal, and their age difference attracted criticism. For nearly a year, they both claimed to be just friends. When Jenner turned 18, they finally confirmed their relationship, posting photos of each other on Instagram. Tyga gifted Jenner a Ferrari for her birthday.
Khloé says the public’s judgment was unfair. “I didn’t think much of the age situation,” she says. “I dated older guys when I was her age. I think all my sisters did. That’s what all girls do, it’s just not so public. There are a lot of people in the industry that are young and dating people the same age as Tyga.”
“You have to put things into perspective,” she continues. “Kylie has to deal with all these responsibilities, but no one wants to treat her as an [adult] when it comes to relationships. But I love that T and Kylie didn’t care. They just did what made them happy. They’re so in love, and I think they’re cute together.”
But Jenner says other people that were close to her and Tyga advised them against dating. “The first year we started hanging out, everyone around him told him not to be with me. I still get comments like, ‘Don’t be with him.’ But we’re not doing it for the public—we love each other. We need to be together at all times. We never get mad at each other, we just figure things out.”
When Tyga and Jenner arrived at her photo shoot, they walked in shoulder to shoulder, with Jenner playfully tugging at his black T-shirt. Later, she walks him to the door and kisses him goodbye before he leaves for a few hours to see his son, King. I tell Jenner that her face lights up whenever she talks about him, and her response is adorable. “Really? Oh my god, stop!” she says, flushed. She doesn’t admit outright that Tyga is her first love—“Well, you have those childhood loves when you’re, like, 14”—but she explains this is her “first real, mature relationship.” (In September, she revealed on Snapchat that he gave her a promise ring.)
Jenner, however, also confirms the tabloid reports that she and Tyga went on a month-long break this past May. Denying rumors of Tyga’s infidelity, Jenner insists they spent time apart because “I just needed to see what it was like not being with him.” In the end, she says, “we realized that wasn’t what we wanted.”
During their hiatus, there were rumors that Jenner and Drake-affiliated singer PartyNextDoor were a couple. When asked if they ever dated, she pauses. “He asked me to be in the ‘Come and See Me’ video, and that was after Tyga,” she says. “Me and Party have a cool relationship. I think he’s so talented and I love his music. But I wouldn’t say we dated. It never really got to that boyfriend-girlfriend stage. It was just fun. I was doing what I wanted to do.”
As for her relationship with Blac Chyna, Jenner says there’s no beef or awkwardness, despite media reports of tension between her and the Kardashians. The day we met, Jenner, after talking to Tyga about Chyna, texted her to check on how her pregnancy was going. Chyna called her the week before and they were on the phone for an hour. “I never fought with her over social media in the beginning, but I understand where she was coming from and what place she was in,” Jenner says. “We’re totally fine. It’s all love.”
A few years ago, Khloé sat Kylie and Kendall down and imparted on them what she considers the best advice she has given her younger sisters. “I said, ‘You have your entire lives to be old, but we’re only young for a few years, so embrace that. This is your time to make mistakes,’” Khloé recalls. “I hate that in this world everyone’s being watched and you don’t feel like you can make mistakes. That’s the point of growing up.”
It’s true: Unlike a regular 18- or 19-year-old, Jenner wouldn’t be able to get a fake ID or drink illegally without subjecting herself to public scrutiny. In the past, she has said that her biggest fear was reading awful things about herself on the internet, but she makes it clear that she has gotten over that phobia. “You can’t please everyone.” She shrugs. “I just want to live my life. I have nothing to hide anymore.”
Right now, Jenner simply wants to focus on Kylie Cosmetics. “I want to be as big as the other [cosmetic] brands. It’s my dream to be on Forbes.”
Growing up, she didn’t think being a businesswoman was a “respectable” title. “I never heard people say, ‘Oh, I want to be a businesswoman when I’m older.’ It was usually a nurse or this or a that.” But seeing her mom and sisters become successful entrepreneurs showed her otherwise. “My mom has been a huge influence on me; Kim has done amazing things. I look up to all of them.”
Jenner thinks it’s cool that she is considered by some to be the most famous Kardashian. She’s aware of how much of an influence she has on teenagers and knows she’s a role model for some. “Sometimes I’ll be typing out a cuss word and I’ll be like, ‘I can’t say that! There are probably kids watching.’”
But unlike Kim, Kourtney, and Khloé, Kylie says she hopes to have a short stay in the spotlight. “They started later than me,” she says, “but I just know that this life isn’t for me forever.”
She agreed to appear on Keeping Up With the Kardashians when she was nine years old, but says her family had no idea how massive they—or the show—were going to become. Looking back, she’s not entirely sure she made the right decision. “If someone told me how big it was going to be, I probably would’ve had a second thought about it,” she says. “I don’t want to be ‘Kylie Jenner.’ It’s become a job more than who I am. I don’t even want to be that person anymore.”
Although she’s not sure she has any other choice. At Chateau Marmont, when asked if she will ever be able to fully escape the spotlight, Jenner leans back on the mustard yellow, velvet Victorian couch with a confused look. “I don’t know,” she says, scrunching up her face. “Is that even possible?”