A Day In The Life Of Kylie Jenner's BFF, Model Jordyn Woods

Ever wondered what it’s like to be in a celebrity’s inner circle? In our series The Plus One, Arianna Davis offers a peek inside the world of assistants, backup dancers, BFFs, and other right hands to the world’s buzziest celebs. Check out the last instalment here.
When the elevator doors open into the lobby of New York’s Public Hotel one August morning, it's unclear if the Jordyn Woods who's about to arrive will be the edgy, wig-wearing bombshell best known for sharing sultry solo shots with her 3.3 million Instagram followers, or the bubbly, baby-faced co-star of the E! docuseries The Life Of Kylie, where she plays a sweet sidekick who’s always down with her BFF.
On this day, it turns out it's the latter. Woods strolls out of the elevator alone, wearing a flouncy floral dress and furry slides. Her hair is slightly messy, and she’s wearing no makeup; her only accessories are a Cartier bracelet and iced coffee. There’s no excessive lip kit liner, or camera crew, or continuous Snapchatting, just a chatty 19-year-old girl with wide eyes, a slight case of vocal fry, and a habit of pulling on pieces of her blow-dried hair as she speaks.
The daughter of a stay-at-home, entrepreneur mum and a television sound engineer father, Woods grew up in Oak Park, California, before she moved to Calabasas at 13. That’s where she met Kylie Jenner. But unlike many of her Instagram followers seem to believe, Woods is not just an entourage member, or a freeloader. Two years ago, a Wilhelmina Modelling agent contacted Woods after noticing her on Instagram, and she’s since quickly become one of the fashion industry’s most in-demand plus-size models. And she's also a designer: On September 11, she’ll debut a collection she designed for curvy girls in collaboration with Addition Elle, a week before she turns 20. And while she diplomatically answers my Kylie-related questions throughout the day, Woods never hesitates (with a mean side eye) to make it clear that while Jenner is her best friend, this is her story.
She’s surprisingly blunt ("I'm too busy to watch TV"), and mature for 19, often dropping gems about the power of attraction ("Sometimes, you literally just have to ask the universe for something") and the meaning of fame ("You can have millions of people following you; that’s not success, that's fame"). She’s still a teenager at heart, though, so by the end of our day together, our little crew — myself, her publicist, and our photographer — begins to feel like a high school clique, despite the decade age difference between its oldest and youngest member. We’ll get emo while listening to SZA, agonise over boys, and get manicures (obviously). Woods will also open up about the death of her father, admit that she became a spokesperson for body positivity by accident, and, yes, talk about what it’s really like being Kylie Jenner’s best friend.
But first up in a day of Jordyn Woods’ life? Makeup, of course.
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As soon as we step foot in Woods’ hotel room — she’s in town for a few appearances to promote her Addition Elle line, as well as the Panorama Music Festival — she announces she has a new makeup routine that she’s excited to show us.

“I was a tomboy growing up,” she says. “I never cared about this stuff until I started to hang out with girls who wore full faces of makeup.” (It would be kind of hard to avoid becoming beauty product-addicted when you're friends with The Lip Kit Queen and a crew of models that include the Hadids...)

"And then I was like wait, I need to get in on this! So I mostly learned from friends and YouTube, and I became obsessed. But now, I’m starting to realise less is more. I always start with my eyebrows before anything else. After, I just take my concealer and go in and clean them up and sculpt. That way people can’t tell if you haven’t had your eyebrows done in weeks!”
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Post-brows, Woods finishes up with NARS concealer, a creamy Tom Ford bronzer for some glow, a little bit of blush, and a brown Dior mascara for her lower lids (none on top, because she has lash extensions). And, of course, some Kylighter. (For the uninitiated, that’s Kylie Cosmetics’ highlighter.)

As she gets ready, she laughs when her stomach rumbles.

“I’m a vegetarian now as of like a week ago, because I watched that new documentary What The Health,” she explains. “I started off wanting to be a vegan and then I decided that skipping meat is pretty easy for me, but dairy is a lot harder. I’d eat a cookie or something and not realize there were eggs in it. Even pasta dishes have a lot of dairy! Sometimes I’m just too hungry to be picky. But yesterday I ate a plate of grains and kale with a side of French fries for dinner. I want to eat healthy, but I also want to eat things that are delicious and also feel full.”
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One of the first things I notice about Woods is the way her light brown doe eyes and shy, gap-toothed smile contrast with a noticeable smattering of tattoos across her body. She’s got nine, including this one down her spine, which she got when she was 17, depicting the seven chakras of the body. There are also two connected triangles in her inner left arm which represent balance and equality, an ode to her Libra astrological sign. Her latest ink was done by her oldest brother, Joshua, an L.A.-based artist.

“I got it two weeks ago, in memory of my dad,” she says. “It’s a J on my side with a little halo in white ink, so you can’t really see it. That felt meaningful.”

Woods also has a younger brother, John III, and a younger sister, Jodie, who’s 10; for most of her life, she was the middle child until her baby sister came along. Woods says Jodie already has big dreams of being a YouTube star. “Like all the kids today,” she jokes.
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The vibe in Woods hotel room, where she's been staying for nearly a week, is very relaxed. She doesn’t seem to mind the intrusion of a writer and photographer, and the area near her bed feels surprisingly homey; SZA’s album “Ctrl” is playing in the background. She hums along to the tune “The Weekend” (“My man is my man is your man/heard it’s her man, too”) as she applies some raw shea balm butter to her elbows and knees. “Yes, I’m Black, and yes, I get ashy,” she says with a smirk. “Shea butter is key!”

Next, she’s ready to get dressed for the day. “What’s my outfit vibe? Cozy? Summer?” she asks her closet. She walks back and forth between the closet and her mini-shoe collection, mulling over a pair of Spice Girl-esque platform Doc Martens, Vans, or the rubber Adidas that she just purchased. She pulls out a few options, including a white latex top and a lightweight, bright orange trench. Eventually, she settles on a white linen TopShop crop top that she ties near her belly button and a pair of checkered pants. The finishing touch is a spritz of vanilla body spray from Victoria’s Secret. “Nothing special,” she says with a shrug. “I’m a simple girl.”
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I will soon put together that reinvention and self-discovery are common themes in Woods’ life right now; aside from her new makeup routine and vegetarian diet, there’s one more thing:

“My nerd table!” she claps. “I took a semi break recently. I had started filming the show with Kylie, and then my father passed away. I just couldn’t take a lot of castings or do a lot of traveling and jobs. So I started picking up hobbies. It feels like a new way to get to know myself.”

There’s the DJ table, which she purchased two weeks ago. “I already have a big one, because I like to experiment with DJ’ing. But it’s still in the box because I travel so much, so I haven’t been able to use it. This one is more portable. I’m teaching myself, and it’s going okay." I'd venture to say it's going more than okay; a few days after we meet, Woods DJ's an event for True Religion, and in October she's spinning at a Wilhemina event for World Smile Day.

"I grew up on a lot of R&B; my mum listened to a lot of Sade, which I didn’t like as a kid and now I love. I’ve been listening to a lot of Amy Winehouse, and SZA, obviously. I admire her because she’s slowly progressing as an artist. She respects the process, and the fact that you can’t just start off as Rihanna. You have to get there.”

And then there’s the sunglasses collection; she tries on each pair, asking our opinion on which shades to wear for the day. “I literally just became a sunglasses person,” she says. “I’ve noticed that the more I think about something, the more I attract it into my life. One day I kept saying ugh, I have no sunglasses. And now I have an abundance of sunglasses that I kept randomly finding.”
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Woods is a natural in front of the camera, with an ease with herself that seems much more confident than the average teenager. But like anyone, she admits, she also has bad days — and that, she says, is one of the issues with social media. The world only sees the good ones.

“I look at my Instagram and think, ‘I wanna be Jordyn sometimes, too!’ It’s hard being a teenager, no matter who you are, because with social media, there’s so much pressure. Kids now are skipping the awkward phase; they’re 11 years old with a full face of makeup and lash extensions! It’s so much pressure to fit society’s standards. I was always a tomboy, always fit in, but never really fit in. I felt like I was different. And I still feel like I am, but now I’ve realised it’s cool to be different. I want to be the outcast. Your individuality is a gift.”

Before changing for the day, Woods takes one last snap in her dress, which is by Realisation, though she says she had no idea when she bought it that it was an “it brand” right now. She got her hair blown out yesterday, so that doesn’t require much fuss.

“I don’t dye my hair, and I’m actually taking a break from wigs,” she says. “I actually had a dream last night that I dyed my natural hair blonde and then it fell out. I don’t know why I had that dream, I wasn’t even thinking about hair before I went to sleep…”

The obvious next step is to Google the meaning of “hair falling out dreams.” Woods’ face looks horrified as she reads.

“‘To dream that you are losing your hair denotes that you are concerned with getting older and losing your sex appeal...’ Okay, this is totally off,” she laughs. “I’m pretty sure that dream was more about me thinking about going blonde. I don’t care about getting older. I’m getting better with time!”
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Woods’ smile turns sly when I ask her about the bouquet of flowers and brand new Gameboy on her “nerd table.”

“The guy I’m dating got the Game Boy for me,” she says, her voice audibly climbing up an octave. “The flowers are from my publicist. The guy I’m dating would definitely not get me flowers. A Game Boy is so much cooler! I had mentioned wanting one, and he was getting one for himself, so he got one for me, too. I play Mario Kart, and there’s a two player option on here. I played it on the plane ride over...”

When pressed, Woods shares a few more details, though she won't give up a name.

“It’s very innocent, it feels like we’re great friends. We met at a music festival where he performed two years ago. We didn’t really talk, and then I saw him later at Coachella, and we didn’t talk then either. But then one day we started texting and that was it.”

She adds that in her friend group, she’s always been the single one, so dating someone regularly is new for her.

“All of my friends have always been obsessed with boys and wanting to be in a relationship, but I don’t necessarily want to be in anything serious. I mean, I’m 19! I’m not going to get married. I’m busy, and he’s busy, which I like. Of course I want you to be obsessed with me and want to be with me all the time. But if you were actually with me all the time, I probably wouldn’t be into you.”

She pulls out her phone to show us a photo E! had posted yesterday of her and Fai Khadra, a singer and long-time crew member of hers and Kylie’s. In the picture, Woods and Khadra are walking down a Manhattan street holding hands; Woods tweeted the shot with the hashtag #NationalGirlfriendDay. I ask if this was purposely a move to make the guy she’s dating jealous, or if she’s just trolling herself — or her fans.

“I mean, I’m not in a relationship! We’re not together, and I was just having fun,” Woods says. “Fai is cute, but it’s not like that all.”

Before we head out, I notice there’s one more thing on the nerd table: A brand new box of Legos, which she got for the guy she’s really dating. Flowers are so not Generation Z.
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Another one of Woods' latest hobbies is photography. She explains that just the day before, she'd gone over to B&H to buy this used camera for $150, then asks our photographer for some tips on aperture.

Still, her career in front of the camera is just beginning. So far, she's been the face of a line for Torrid, walked in shows for designers like Christian Siriano, and in addition to the upcoming Addition Elle line, this September she'll be the official Fashion Week correspondent for E!

“I get comments every day that are like, ‘What does Jordyn Woods even do?’" Woods says. "They see the cool stuff, but they don’t know how hard I work. They don't know that I often book gigs that don’t pay, or that I sleep in the tiniest hotel rooms, or that sometimes I get absolutely no sleep. I’m not a complainer, because it’s all worth it, but I work hard. I understand that you can’t just start at the top. I don’t think that I’m famous, and I’m not trying to be. I want to be successful. You can have millions of people following you; that’s not success, that's fame. But success pays your bills, success means you’re comfortable, that you’re happy. That’s success to me.”
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In the car ride over to her modelling agency, Woods mentions that she was homeschooled. I ask if that was by choice.

“I’ve gone through a lot of stuff that people don’t know about,” she says. “My dad lost his job for a while during the writer’s strike, and then my parents separated, so I moved around a lot. There was one year where I moved like, four times in one year. When I moved to Calabasas, I decided to do home school. I don’t regret it; I did have normal high school friends, and I did go to homecoming. I didn’t go to prom, though. But I did shoot a modelling campaign for prom clothing, which made me feel like I went.”

She adds that she and Kylie also recently took a student who needed a date to prom, one of the storylines in the first two episodes of The Life Of Kylie. She also didn’t really have a graduation; she was doing modelling work when her high school diploma arrived in the mail.
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Walking down the street toward Wilhelmina, Woods takes a puff from a vape (“It’s not weed!” she promises) that smells like maple syrup. “This is disgusting!” she says before thrusting it back into her bag. Out and about, she blends in like any New Yorker, and says she rarely gets recognised, either here or back in L.A.

We’re in the middle of a typical day in her travelling, working life, but I wonder: What’s a real day in her life like back at home?

“I live with my best friend” — that’s Kylie, she clarifies — “and, I don’t know. It depends if I have to work or not. If I don’t, we’ll just hang out with the dogs. I’m like their godmother. I try to do something active every day, like hot pilates or going for a walk. I’ll get some food, a smoothie. I’m very basic. I used to turn up a lot, but in my old age, I’ve settled down.”
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While she’s waiting for her agent, Woods takes a social media break. (I’m surprised to realise this is her first real one of the day, but she swears that she’s not a big Snapchatter or Instagrammer.) Suddenly, Woods has bangs; she explains that they happened by accident.

“The one time I did bleach my hair blonde, some of my hair broke off. It wasn’t intentional. I just got my hair done yesterday, and now these pieces look like bangs. I push them forward when I want to look a little emo.” She then curses about her acrylic nails, which she’s dying to get off. “We need an appointment,” she declares, tapping at her screen to shoot a text message to her favourite place’s owner. And poof, just like that, we’ve got appointments at Bling NYC. She looks down at her nails again. “I can’t wait to take these things off and go natural.”
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Woods’ agent is thrilled to see her, embracing her as soon as she sees her and pulling her into the photo studio to snap some digitals for her portfolio. “It’s rare that we get Jordyn in New York, so we have to take advantage!” she says as she snaps away. I comment to Woods that with how comfortable she is in her own skin, I can see how she’s become a champion for body positivity.

“It happened naturally for me, almost by accident,” Woods says. “I never was all ‘Body positivity! Love your curves!’ People just saw that I had confidence and happened to have curves and they were like, ‘Oh wait, this girl is body positive,’ because I reflected that way. I never went out of my way to be like this. But now that I have this platform, I’m going to do it.”
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Her collaboration with Additional Elle is part '90s punk, part medieval, part Michael Jackson-chic, every piece intended to fit a curvy girl’s body, from flowing tops to plenty of denim.

“I don’t think we need to even use the term plus-size, I think sizing should all just be one,” she says. “I was talking to a girl much bigger than me, and she was like, ‘I don’t even look at you as plus-size.’ There are so many shapes and sizes across this spectrum. I went to a casting in L.A., and they asked if I’d consider wearing pads to make me look bigger. My agency had told me that might be something that would happen, but I couldn’t believe it. I don’t want to wear something to fit your clothing, because the whole point is that your body is made how it’s supposed to be. But there are a lot of social media trolls who will say they can’t believe I’m doing plus-size work. It’s like, I can’t win: I’m too big, I’m too skinny. I’m not getting booked for regular runway shows, because I’m too big, but then some people think I’m too small for plus-size. Why do we even have to differentiate?”

“I never wanted to model. When my agent reached out to me from Instagram, I thought it was a fraud, because my friend had gotten a similar email a few weeks before, and it turned out to be fake. But I love it. When I was really young, I wanted to be a doctor. At 14, my email had Stanford in it, because that was my dream. But after my father got sick, I started hating hospitals. And then modelling just fell into my lap. I still get lost sometimes about what I really want to do long-term, but I’m very creative. That’s why I have all these passion projects and hobbies in my life. I want to keep making myself better.”
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On the walk to lunch, Woods points out that her not-boyfriend hasn’t texted her all day. It’s 2 p.m. She asks if we think it’s because of her tweet; we reassure her that he must be busy and will probably text. (Spoiler: He does, not too long after, and when the text comes through she giggles like...well, a teenager.)

Kylie Jenner’s best friend must struggle with dating, I say. How can you ever know someone’s true intentions?

“I’m always worried about people’s intentions,” she says. “But not too much, because I feel like I can tell instantly if someone is weird or not. Especially with dating guys, I know so many of them want to be able to be like ‘Oh, I’m talking to Kylie’s friend, or I just want to be in the friend group,’ or it’s someone who wants to lowkey be famous or do music, so they just start talking to me to see what they can get out of it. That’s how most people are, so I’ll try to feel anyone out for awhile before I start trusting them. I think that’s one of the reasons why I really like this guy. We’ve been talking long enough, and he’s not really on the scene, so I don’t feel like he’s up to anything.”
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After some debate about local options that are vegetarian friendly — Chinese? pizza? — we settle on Sarabeth’s, an NYC staple. Woods stops in front of the restaurant and poses for a picture for her Instagram; inside, after she orders grilled cheese and tomato soup with a caesar salad, she starts the Instagram filtering process. (In the photo editing app VSCO, for the record.) She decides on making the picture black-and-white, because she wants something different.

“I feel so ready for change,” she says, coming back to that same common theme. “Every part of your life is full of ups and downs, so I think you have to be ready for change. My dad passed away at the beginning of the year, and that’s something I never imagined would happen to me at 19. You never know what life is going to throw your way.”

I press gently about her father’s passing and how she managed to deal with that while also being in the public eye. She takes a deep breath and a few moments before answering.

“I actually went through kind of a scandal that made everything worse. My dad was in the ICU for about two months; he had meningitis and they kept treating him and doing MRIs, so the hospital bills were insane...the first one alone was like, $200,000. No one has money like that just ready to go, at least my family. So they made a Go Fund Me to raise money, and of course I wanted to post it, because I have a substantial amount of followers. Well, it turned into people attacking me, saying ‘Your best friend is rich, why would you post this, this is a scam, you’re robbing your fans, you killed your dad for money.’ They were pointing out the nice things I own and saying I should sell them, and leaving snake emojis in my comments.

“I was doing something simple to help my family, and it caused me to ask myself: Was that wrong? To ask anyone who was willing if they might want to help my family? I turned off my Instagram comments for weeks, and it just made the entire grieving process even more difficult. I understand why people might come to certain assumptions, because I put my life on social media, but I think people went about it the wrong way. I mean, my father died. Is there nothing left that’s going too far?”
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For all of her talk of fashion and beauty and lighthearted jokes, it’s clear Woods is, still, indeed grieving. She talks about her dad a lot, explaining that he did the sound engineering for The Fresh Prince Of Bel Air — which explains her casual #TBT on Instagram with her and Will Smith where she calls him “Uncle Willy.”

“The Smith family has known me since I was still in my mum’s stomach!” she says. “I have a couple of best friends, and Jaden is one of them. He’s actually here in New York, and we’re going to hang out when I’m done working today. I think for most people it’s not normal to stay friends with the kids you grew up with, but somehow we’re still friends and love each other. I think it’s really hard to maintain long term friendships, especially when people always have an opinion about you or your relationship.”

Kylie, her best friend since middle school, is also someone she considers she’s grown up with. But she says that staying close and keeping their friendship authentic has never been an issue.

“A lot of people are just friends for the 'gram. Like, ‘We’re both bloggers, so let’s hang out and pretend to be cool and take photos the whole time and blog each other.’ I’m very much the opposite; I hang out with someone because I’m enjoying myself. I think Kylie and I have continued to have a good relationship because we think so much alike. I was actually just talking to her last night about how I realised that not everyone thinks like me. Sometimes you forget, like you get upset and wonder why someone reacted the way they did, and it’s like well, this person wasn’t raised like you, or maybe they didn’t get a lot of affection growing up, and parenting plays a big role, where they grew up, their morals, how they look at life. No one thinks exactly like you. But Kylie and I are both very logical and and we just have a connection. Not everyone is going to get you, so when you find someone who does, you have to hold on to that.”
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At the nail salon, the owner, Anna, embraces Woods and asks how Bella and Kendall enjoyed their manicures on Sunday. Casual. Woods sits with the gel color palette for awhile before deciding on a similar nude. “I’m boring!” she says. “I think everyone would be surprised to learn that I’m pretty regular. I think they’ll see that on the show.”

The Life Of Kylie, it turns out, was not something Woods was dying to sign up for.

“I didn’t want to do the show at first. But Kylie and I are a big part of each other’s lives, so if it’s about her life, I’m a key player, so I’m not gonna just not come around. I figured, being with her all the time is already my life, so we might as well do it. And it turned out to be really fun, we’re just super silly on the show.”

Here’s the part where this interviewer, who has already asked plenty of Kylie questions, asks: Does she ever get tired of being asked about Kylie?

“Yes. It’s not that I don’t love Kylie to death, but it’s just like, if you want to know about Kylie, you should just interview her. If you’re just going to ask me questions about her, why don’t you just talk to her yourself? I have so many things that I’m doing that I would love to share. If I’m promoting something, I’m not there to talk about anyone else other than myself and what I’m doing. I understand why people ask about her, because she is very popular and people want to know about her. And I love it. But I’ve got to focus on me, too.”
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After spending six hours together, midway through our manicures everyone’s energy starts to wane. Woods says she’s ready for a matcha tea and some relaxation before she hangs out with her friends, Jaden included, later that night.

But before we go, I have to know: She’s a model, fashion designer, and social media star, all before she’s even reached 20 years old. What’s next?

“My dad worried that I was growing up too fast,” she says softly. “That’s something that I think about. I still remember all of the advice that he gave me. And my mum is my manager, she keeps me grounded and guarded and I learn from her by experience, because she’s so strong and a hard worker. At the end of the day, it’s all about family. So I have no idea where I'll be a year from now, five years from now. I'm taking things one day at a time. I just want to be able to provide everything that I can for my family. If they’re good, I’m good. Isn’t that everyone’s goal? To not have their mum ever work again? Well, that’s mine. And we’re getting there. We’re not there yet, but almost.”

She lifts up a hand to regard her new, natural nails. And then she looks right at me.

“Hopefully, I’ll be there by 25. I got this!”

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