With the face of an ingenue and a figure that’s reminiscent of a starlet from Hollywood’s Golden Age (luxurious curves), Kailee O’Sullivan sits patiently as the make-up artist preens her face. We’re afforded expansive views of the Pacific from the terrace room at San Francisco’s famed Cliff House but despite all the warnings of a storm and the crashing waves, the sky is already visible and the natural lighting perfectly adjusted for a photoshoot.
Jane Yu: What was it about you that made your mother push you to become a model as opposed to something else when you were young?
Kailee O’Sullivan: Well, I wouldn’t say she necessarily pushed me to become a model but she kind of was the one to push me to be more out in the limelight. I always wanted to do acting and I like being in front of the camera but I was always very shy. My mother was the one who kind of pushed me in that direction when I wasn’t really able to push myself. I would have never gone to an open call or a casting for modeling if my mother wasn’t the one saying, you gotta do it, you gotta do it. So, I’m grateful for her doing that in that sense.
JY: Is modeling your happy medium? How come you decided to pursue modeling instead of theater?
KO: Well, I did do some theater on the side in high school and I did study acting in school after in a few different colleges but modeling just sort of picked up by itself without me even trying too hard in the beginning. It really seemed like it was kind of meant to be because it just took off in its own direction. And then after that I kind of took the bull by the horn, as they say. I went with it and then made it my own instead of just riding the wave. I showed up being more myself, but not just like a young, little girl or young teenager in the industry who doesn’t really know what’s going on but more somebody who knows what she wants. “This is who I am. Here I am”– let’s work, that kind of thing. And it became a lot more fun and a lot more creative and a lot more adult. I felt like more of an adult.
JY: How old are you now?
JY: And you said you studied theater after college?
KO: Yeah, I studied theater a little bit in high school.
JY: What was your major?
KO: In college? I never finished my degree. I’m kind of in and out still to this day but I’ve been studying acting and photography and writing.
JY: Creative writing?
KO: Yeah, creative writing.
JY: Cool. Creative non-fiction?
KO: Yeah, non-fiction. I don’t really… I’m not a fiction writer.
JY: What would be your alternate profession?
KO: I definitely want to do more acting. I want to be an actress just as much as I would like to continue modeling. But I definitely want to be in the acting field a lot more. And then on top of that I do have a huge interest in like, anthropology, cultures, communities, tribes around the world. I love traveling so in some ways. Somehow, eventually, I’d like to incorporate that into projects and to my career. Maybe do photographs and stuff like that.
JY: Is this your outfit today?
JY: Boho chic–I like it. You look like a traveler… How much of your clothes has been influenced by the clothes you model from brands?
KO: I definitely think it’s influenced me to enhance and show off my curves more but in a very subtle way. It’s not always where I’ll model something and think, “Oh, I wanna wear that.” It’s more, like, over the course of doing this for over ten years, seeing different women and different body shapes expressing themselves through their clothing.
JY: So you’re into the silhouettes and…
KO: Right, so seeing how different women dress over a ten-year-period has influenced me more in a subtle or gradual way. Sometimes I’ll see something someone’s wearing and I’m like, oh, I want that but it’s rare… it doesn’t happen that much. It’s opened me to a world of how women can dress from a young age. I do have a totally separate style and taste, too.
JY: How would you describe it?
KO: I’m drawn to textures and colors. And also something that flatters my body in my shape, personally. So even if I like something that is very trendy at the moment, I can say easily, well, you know, it’s beautiful but it’s just not for me. Like, I’m not gonna wear that. I’ll also wear something that’s not trendy, maybe, but something out of style I know that I look good in and I feel good in it. So, yeah, it’s just kind of eclectic. I definitely like colors, textures, fabrics–anything very natural. I like everything to be very natural looking and feeling.
JY: I don’t know too much about the modeling industry, but it seems like some models are more typecasted into one type of look.
KO: Let me think about that.
JY: In your pictures, there seems to be a variation to the outfits you wear and the looks you pull off.
KO: Right, yeah, that’s true. I think there’s a lot of glamour in the industry which I think is a wonderful thing. You know, I think everybody looks gorgeous and I love feeling glamorous at times but what there isn’t so much in the plus-size world is a more pared down, very natural, even naked look. Naked, quote-on-quote.
JY: Do you mean, like, rustic?
KO: Yeah, could be rustic. Rustic is a good word. T-shirts, jeans, just something that kind of shows a woman in her most natural state and how beautiful she can be and I think there’s more and more of that now. It’s coming up but I’ve always loved somebody who looks very understated. I love a glamour look but I also like to see the more understated, just so that the natural beauty of the woman shines on its own. So, that’s more of my style and I think I see it from time to time but not as much as I’d like.
JY: Is there something you wish that people knew about you since you say you’re people-shy?
KO: Yeah, I’m shy but I’m also a Leo who definitely likes to be in front of the camera. There’s a dichotomy within me or a duality where I am very private but I feel like there’s something in me that I want to show, that wants to be seen. I can’t wait to get it out and show it. It feels amazing and it feels creative and it feels like it’s an expression of the self.
JY: And how do you feel about New York or specifically, Brooklyn?
KO: I love Brooklyn. New York’s always changing which is really hard because you get attached to a certain place or certain neighborhoods, certain group of people, but the nature of New York is transient and it’s sad because it’s become more and more modernized. On a daily basis it’s becoming more modernized and a little bit more homogenous which is sad. I wish it would stay a little bit more mom-and-pop.
JY: When you say New York, though, do you mean Manhattan or Brooklyn or both?
KO: Manhattan mostly but Brooklyn for sure is on that incline, that path and all five boroughs are eventually… like, people just keep getting pushed out of their neighborhoods ‘cause the rent is so expensive.
JY: Did you originally live in Manhattan?
KO: No, I’m originally from about a half an hour east of Manhattan, on Long Island.
JY: And you were born there?
KO: I was born and raised in Long Island which is beautiful in its own way but definitely a lot quieter. New York will always be my home. I love it there but I also love to travel so I like to go away and come back.
JY: Do you watch the [HBO] show ‘Girls’?
KO: I love ‘Girls.’
JY: What are your thoughts on how Lena Dunham kind of pushes the boundaries and standards of beauty?
KO: Yeah, I’m all for it. I absolutely love everything she has done and I do hear a lot of her backlash and a lot of things that people don’t like. And I hear it. I understand. But,personally for me, we need somebody like her, and not just curvy women. Somebody who’s willing to just show all of her flaws in such a confident way. To me, it doesn’t feel forced or even too in-your-face. There’s nobody else out there who’s willing to make such a fool of themselves at this age and say, “Hey, this is okay. This is so okay. I’m struggling, I’m in my mid-20s. I don’t know what the hell I’m going to do with my life.” I think we’ve all been there. We’ve all been lost, we’ve all been struggling. We’ve all struggled. I mean, I think we need somebody who’s like a champion for that, to show that it’s okay. Every episode of that show I’m, like, “Oh my god, there is somebody like me and my friends!” We all find common ground with her.
JY: Do people in Brooklyn find that show to be an accurate parallel?
KO: Yeah, I think it is. There’s a lot of backlash about how there’s all this nepotism and also that the characters are spoiled. But I think if you watch the full show, if you watch all the seasons, you see that, yes, they are spoiled but this is their big wake-up call. Like, they might not have had it so hard growing up but eventually the red carpet gets pulled out, yanked out, from underneath you. Your parents shelter you growing up if you’re lucky enough but then eventually, especially if you’re living in New York, you have to learn how to live on your own. You have to learn how to hustle and struggle and nobody’s there to really catch you when you fall unless you build a group of friends which is the best part of the show. You see their own little community, their own little tribe. I think if you move anywhere long enough you’re going to develop all of that and that’s so important when you start to create your own life outside of your parents’ house growing up there. I love everything she’s done. I think she’s amazing–so smart and intelligent, brilliant.