The Reinvention of Kylie Jenner

Among the many things the Kardashian-Jenners are known for—enviable commercial instincts, unswerving loyalty, astounding ubiquity—lavish birthday gestures surely rank near the top. They have been throwing money-no-object parties for so many years, since long before they were famous, that entire industries have sprung up around them. If you count all the siblings, parents, grandchildren, significant others, and exes who are still in the picture, that's something like 25 birthdays a year, which, mathematically speaking, is one every 14.4 days. The reality for everyone in the family is only slightly less rigorous. For example, the entire month of September is a rare birthday-free zone on their calendar. November, on the other hand, abounds with cakes and balloons—four celebrations (Kendall, Rocky, Kris, Dream) in the span of a week! And then there's August, which Kylie owns.

Indeed, Kylie and I are on the phone the very Thursday of the party she's throwing for herself later at her concrete mansion in Beverly Hills, even though her birthday isn't until Monday. "I'm pretending my birthday is today because I'm going away tomorrow," she says. "So we're having a little get-together at my house so that my kids are a part of it." (A "little get-together" in King Kylie's world means a strictly enforced hot-pink "princess kitty" theme with three cakes. See Instagram.) It's 11 a.m., and she's taking a break from her preparations—Stormi and Aire in the background occasionally interrupting—for a meandering conversation about her year of being brave, testing the waters, and pushing herself to spend more time in the flow of normal human life.

For the sake of argument, let's agree that Kylie is the first Zoomer—patient zero of cohort Gen Z. She was born on August 10, 1997, three weeks before Princess Diana died and Netflix was founded. Chelsea Clinton packed off to Stanford that year, Ellen DeGeneres came out on the cover of Time, and J.Lo got married for the first time. The premiere episode of South Park, "Cartman Gets an Anal Probe," aired when she was 3 days old.

In some ways, she embodies many of the quirks of her generation. For example, she has an aversion to small talk. I first met Kylie over the phone in March 2022 as I was working on my forthcoming book, Citizen Kim, about her big sister. I spent years around Kim and had interviewed almost everyone in the family—except Kylie. The call lasted no more than 20 minutes and was the very definition of pulling teeth, a lot of long, awkward pauses and monosyllabic answers. At the time, I took it almost personally because it felt impertinent. Show some respect, young lady. But looking back, I see that it was just a combination of shyness and circumspection.

This time is different—although she still won't indulge me in small talk. (Whenever I share a personal anecdote, she says, "Yeah, same.") Kylie 2.0 is less suspicious and, relatively speaking, effusive. I had read the YouTube comments from the podcast she did with her sister Khloé Kardashian in late 2025, and the very first one said, "1 hour of Kylie just talking. This is what we have been waiting for all these years." And that is when I realized that even her superfans find her inscrutable. When I share this with her, she says, "Sometimes, I don't realize how much I don't share? So when I do things like that, I feel like that's always the reaction." In other words, she knows. She doesn't seem to care about relatability, which is probably the result of having been on a TV show since she was a child. As she said in a recent interview, "Not a lot of memories. I was 9 years old. [Cameras] were there one day in the house." You, too, might not want to bond with strangers after nearly 20 years of reality-show surveillance.

Kylie once said she feels like she lost her most "amazing traits" because she listened to "ignorant people who are bullies" on the internet. Today, she says, "I'm a confident person in my private life. I think it's just hard to be a woman and a human because of this very singular experience of having so much attention."

"She's always been the most, I would say, individual of all of us," says Kim Kardashian. "She's always known what she wanted to do in life, always known who she is at a young age, and has always been very confident. She's a wise soul. I've always seen that side of her behind the scenes. But she's coming into her own, and I think the world can see what our family has always seen."

One of the occasions for this profile is the rebrand of Kylie's accessible, collab-centric fashion label, Khy, into wardrobe-first minimalism. In addition to the launch of its upcoming fall collection, Khy is expanding into shoes for the first time in a collaboration with the Italian label GiaBorghini, which launched August 21. (More on this later.) But I could not help but think that it is Kylie herself who is in the midst of a rebrand. She is suddenly popping up on podcasts, acting, and sitting for interviews for British Vogue and Vanity Fair.

"I think it's more of a personal refresh," she says. "I think there's something that happens when you're turning 29—I'll be 30 next year—and you almost feel like the clock is ticking, even though you're still so young. So you're trying… I'm trying… I don't want to look back on life and be like, There's things that I wish I did when I was younger. Even though I already have children—so young—I feel like I lived such an adult life when I was young, and I'm trying to make sure that I don't have any regrets and to do brave things and give myself more opportunities or take advantage of the ones I have." She goes quiet for a minute as I learn in real time not to rush her. "Kim inspires me in that way because she does a lot of things that excite her but, at the same time, scare her. And it's amazing to watch her achieve and chase her dreams. I'm just trying to do more things, choose a few things a year, get out of my comfort zone, and just go for it."

Can you describe your comfort zone? "I think I've gotten really good at protecting myself and knowing what feels really safe and what I can handle," she says. "So I just kind of know—even down to how to leave my house and the safe places to go to. You know what I mean? How I present myself on the internet, what to say. I think there's a lot that I do to protect myself, and I just stay in this comfortable bubble. And I think it's because I've been so judged on the internet. Now, I have this big fear of embarrassment or something—more than ever. When I was younger, I just didn't really think about it. So when I was 16, I put myself out there, and I shared a lot more of my life. But the world is just different. Now, there's all these platforms. There's TikTok, Reddit, Substack…"

I'm afraid to start a Substack, I say. What if no one subscribes?

"I'm kind of into it," she says. "I might start one. It seems fun."

There were glimpses of the new swashbuckling Kylie last year. My first clue came in June 2025, when a fan asked her on TikTok what she requested when she got her "boobs done" because "it's like the most perfect, natural-looking boob job ever," and Jenner, to the world's great surprise, responded: "445 cc, moderate profile, half under the muscle!!!!! silicone!!! garth fisher!!! hope this helps lol." By the end of last year, she did her very first podcast interview in the safe space of Khloé's living room, with martinis in hand. In December, she and Timothée Chalamet went to the premiere of Marty Supreme in matching neon orange. Fun! When 2026 kicked off, the couple (together now for three years) hit the award-show circuit, from the Golden Globes in mid-January (making out!) to the Oscars telecast two months later. Then she appeared on the cover of Vanity Fair smoking a cigarette in a bustier and Hermès riding jodhpurs in a Madonna by Helmut Newton homage. In April, she was the first guest on the new podcast Big Bro With Kid Cudi—entirely winning and hilarious. A month later, she went on Therapuss With Jake Shane and went viral with this flawless bit of repartee: "Sometimes, I think I'm depressed, and then I get a spray tan, and I'm like, 'I was just pale.'"

But the revelation came with her cameo in the Charli XCX mockumentary, The Moment. Vulture described it as the best scene in the movie: "Kylie Jenner, it turns out, has legitimate chops as a comic actress. Nobody tell Kim." When I ask Jenner about it, she says, "I was playing a heightened, bitchier version of myself, so I kind of just turned up the volume." I ask her about the process (Did you rehearse? How many takes?), and she surprises me with a burst of candor and verbosity. "So I got the script," she says. "I was really nervous, so I called Kim, who was doing the Ryan Murphy show [All's Fair] at the time. Do you think I should do this? At first, she was like, 'Okay, just make sure you're prepared for this—blah, blah, blah.' She was a little more iffy. And then I read my part to her, how I planned to do it, and she was like, 'Oh! Kylie! You got this. Do it just how you did it on the phone. It's great.' And it gave me that confidence."

Kim—who, as Kylie said, is "in her actress bag"—was thrilled that her little sister called for advice. "Kylie is so funny," says Kim, "but you know, she was really shy for a while there. I told her that if she was going to do it, I wanted her to be her. So I just talked her through that: Are you gonna be shy? Is this one of those experiences? Or are you going to be you?"

Once Kylie signed up, she spent the next several days running her lines with friends. She felt good enough that she cancelled plans to work with an acting coach. The night before filming, Charli came over to her house, and they rehearsed it a few times. On set the next day, "they shot it maybe 10 or 12 times," says Kylie, "and then I started improvising a bit. It was just these little things that we were playing with and paying attention to what was making everyone laugh in the room, what felt funny." Spoken like a true comedian.

In July, she shot the King Kylie Dunkin' commercial with Dave Meyers, director of untold ad campaigns and music videos. "I had lines, and I had to act," she says, "and even though it wasn't a television show or a movie, I had to act in front of 40 people—all those actors plus the biggest crew you've ever seen in your life. I've never seen more people in a studio before. I was so nervous, but it was a test for myself to see if I could do this or not. Like, can I act in front of all these people? And it was great. So now, I'm like, Okay, I am good to go."

Indeed. The offers have started trickling in. "I haven't found the right thing yet," she says. "There were two scripts that came to me that I passed on. But I read something recently that I'm kind of interested in—the best I've felt about something so far. It's just a pilot; it hasn't been picked up yet. I'm feeling more precious about what I do next because I want to make sure it's the right fit, especially if I'm going to do something major and have to travel and be away from my kids. I want to make sure it feels right."

I tell Kylie that when I started working on the book about Kim—in 2021—I first watched every single episode of Keeping Up With the Kardashians back-to-back over a period of six months, sometimes three episodes a night. "Oh my God!" she squeals. "I'm so happy for you! Isn't it the best?"

It's the most underrated documentary in history, I say, and we laugh.

I bring up the show to tell her that you can see—in later episodes and especially in the Hulu version, The Kardashians—Kylie getting funnier and funnier. Khloé, it seems to me, always held the mantle of funniest sibling. But maybe Kylie is the funny one. "I think Khloé and Rob and I are really similar in that way, but yeah…" She trails off and then whispers, "It's secretly me."

I wonder if she has a theory about what changed. Why did she become more self-conscious as she grew up? Was it getting older and raising children? Caring more about how she's perceived? Or was it something external? "I think social media is a big part of it. It's just changing," she says. "Now, it's more How far away can I get? You know, I delete my apps a lot. I try not to be on my phone all the time. I'm not a teenager anymore. It doesn't feel right for me to just scroll on TikTok all day when I have kids."

Having children so young forces you to grow up fast. You miss out on some things; you become both an early and late bloomer at the same time. Did Kylie experience that? "Yeah, absolutely," she says. "COVID was my college experience—when everything was shut down and no one was really working. It was the first time that I slowed down, and the world started to feel safe again. For the first time in my life, there wasn't a schedule. Sometimes, I feel like a robot, where everything is planned out for me. Khy meetings on Wednesday, blah, blah, blah. But COVID felt like I had a college experience—friends over all the time, and we were always celebrating something or trying to just be together. I was like, 'Wow, I never had that thing of, like, no other outside responsibilities—except Stormi.'"

Stormi was born on February 1, 2018. Kylie was 20. Exactly four years later, on February 2, Aire was born. "I made a promise to myself at 25,” she says, “that I was not going to have any more children—right now—and really just enjoy the last half of my 20s because the first half was like, 'You're pregnant,' and then it's the year of recovery, and, you know, my mental state, my postpartum depression, and all those things. It felt like I lost some of those young years of my life.”

More than once, Kylie says, "I'm almost 30," and it seems to be an indication that she is very eager to exit her 20s. Is there anything she'd like to leave behind? Something that once seemed important that she's changed her mind about? "I think having an enormous life," she says. "I changed my mind about that. When I was younger, I got really excited, and I got the craziest house I could in Beverly Hills, and I just kind of went for it. I've realized that my life got too big, and I said, 'Yeah, never mind.' I think I lost control of my life a little bit for a while there."

The reason for this is almost certainly to do with the fact that she became nearly a billionaire in 2019 when she was just 21. The 10th anniversary of the first Kylie Lip Kit was last November. She was 18 when she posted it to Instagram, and it sold out in minutes. Four years later, she was giving the official video tour of the brand-new, custom-designed pink HQ on Agoura Road in Calabasas with a giant pink neon KYLIE sign and her now-controversial "Youngest-Ever Self-Made Billionaire" Forbes magazine cover hanging in the lobby. (Besides the fact that she wasn't quite yet a billionaire, people got caught in the spokes of self-made. "None of the money I've ever made is inherited, so it's technically true," says Jenner, "but people just feel like the privilege I've had was a major stepping stone.")

Looking back on the 10-year journey, what's the big takeaway? "I wouldn't change it for anything," she says. "I learned so much, and I'm just so happy that I'm still doing it. It's definitely the thing I care about the most. If I had to choose—you can just do one thing—it would be Kylie Cosmetics because it's just such a real passion."

This is perhaps one of the reasons why the early iterations of her fashion brand, Khy, felt like a work in progress—because it was and, in some ways, still is. When the brand launched in 2023, the first collection sold out within days and generated $1 million in sales within its first hour. She admits to me that, unlike Kylie Cosmetics, it wasn't her idea: "It was an opportunity that came to me, and then I realized how much I love it." Earlier this spring, she steered the brand into its new, more grown-up era with a complete creative transformation. "I'm so excited about the future of Khy, and the rebranding is more about creating timeless forever pieces, moving a little bit away from collaborations, and trying to identify just who we are, what we stand for, the clothes that we want to make," she says. "So I think we're still building it, and it's a challenge to build something with so many people watching."

Besides expanding into shoes—which she's been working on for two years—Kylie is most excited about opening a brick-and-mortar Khy store in a couple of years. "For clothes, you really need something physical, a building, to create a world," she says. Perhaps, here, she is taking another page out of Kim's book.

There's a shopgirl legacy on her mother's side that goes back nearly 100 years, to when Kylie's great-grandmother, Lou Ethel, and her great-great-grandmother, a woman everyone called Tiny, opened a beauty parlor in Mississippi. Lou Ethel was the mother of MJ, the beloved grandmother to the Kar-Jenn clan, who died at 91 in July. She herself was the owner of several stores in San Diego for years, including a bikini shop, a women's fashion store, and a children's clothing boutique that was a La Jolla institution for more than 30 years. It's in their blood: When a marriage falls apart, open a shop! Kim and now Kylie, are keeping the legacy alive. "I'm very aware of that," says Kylie, "and I think we absolutely got it from MJ, and MJ got it from her mother—that work ethic and looking up to strong, independent women."

Kylie has gotten a bad rap over the years for not working hard enough, not being a serious person, and people thinking she's not really that involved in her brands. It couldn't be further from the truth. There's always a suspicion about celebrity brands: Is it really her? Kylie set the record straight on Kid Cudi's Big Bro podcast, saying "I go to work every day in the office. I'm super involved and am really crazy about everything. I do the Instagram myself. I do all the posts. I do the marketing, all the shoots, picking the models, knowing all the factories. It's hard for me to hand it off, because it's my baby."

As our conversation is winding down, I bring up Kim's super-viral moment from March 2022 ("Get your fucking ass up and work!"), and Kylie lets out a mordant chuckle. Like Kylie, Kim was born on the cusp of, in her case, the millennial generation: 1980. She is the living embodiment of hustle culture—something Gen Z, like small talk, rejects. Indeed, Kylie once said, "The public will be like, 'You're just like Kim,' and I'm like, 'I am nothing like Kim.'"

Kylie takes a minute to think about what she wants to say. "Kim embraces that narrative about herself," she says. "Because she does work really hard, she's like a superwoman. She just has such a great work ethic, and she handles so many things all at once, which is really impressive." She takes another second, "How I present myself to the internet maybe doesn't show the businesswoman side of me." One more long pause. "So maybe I'll lean into that."

Photographer / Director: Aidan Zamiri

Cinematographer: James Beattie

Stylist: Alexandra & Mackenzie Grandquist

Hair Stylist: Iggy Rosales

Makeup Artist: Ariel Tejada

Manicurist: Zola Ganzorigt

Set Designer: Grace Surnow

Production Company: Object & Animal; Ted & Jane

Editor in Chief: Kat Collings

VP of Creative: Alexa Wiley

Style Director: Lauren Eggertsen

Entertainment Director: Jessica Baker

Director of Production: Erin Corbett