Art and Modelling in New York City

Part I: Modelling

Modelling for Laura Prom 2006

by Heinrich Saint-Germain

It seemed like the height of audacity: to invite Kailee O’Sullivan for a face-to-face chat at the Metropolitan Museum of Art, in New York City.

      But what could be more appropriate? Where better to interview a plus-size model than in a museum—a veritable temple of timeless beauty, a repository of countless artworks honouring the feminine ideal that she herself embodies?

      The timing was irresistible too, as the Met was hosting a must-see exhibition at the time. Titled Art and Love in Renaissance Italy, the exhibit featured Titian’s famous Venus of 1548, on loan from the Prado. But the show was set to close on February 16th, just one week from the day that I sent Kailee the invitation, and I worried that seven days’ notice might be cutting it a bit fine.

      Much to my delight, halfway through the week I received a yes from Miss O’Sullivan, who told me that she would be pleased to get together for a conversation on Saturday, the 14th.

      So there it was: I would be interviewing a plus-size goddess…in one of the world’s greatest museums…on Valentine’s Day. “Dream come true” would be an understatement.

      We arranged to meet at 3 o’clock, but I encouraged Kailee to jot down my cell phone number, just in case something came up. And sure enough, promptly at 3 p.m., as I was waiting in the museum foyer, I received a call from her informing me that the NYC transit system had suffered a catastrophic breakdown, and that she would be arriving 15 minutes late.

      That impressed me so much—that she had the courtesy to telephone and provide an ETA. It was a classy thing to do, and it testified to her professionalism.

      Precisely at quarter past the hour Kailee entered through the front doors of the museum, looking a tad windblown, and all the prettier for it. I introduced myself, and told her my real name. She appeared somewhat surprised, then offered a handshake—which struck me as a very businesslike gesture. I shook her hand warmly while struggling to maintain my composure in the face of such beauty.

Test photo

      Readers, let there be no doubt: Kailee O’Sullivan is even more gorgeous in real life than in her images, and if you don’t consider that possible, then you simply haven’t seen this fairy-tale princess with your own eyes.

      As we made our way to the Met’s elegant Petrie Court Café, Kailee mentioned that just the other day she had visited the Natural History Museum (New York’s other world-class repository of culture), and had loved the experience.

      My heart leapt. Could it be true? A model who enjoyed museums so much that she visited them for the sheer fun of it?

      There could not have been a more propitious omen for our discussion.

* * *

      The bright, spacious café was filled to capacity when we arrived, with not a single table free. There was, however, space at the wine bar, which is where we settled ourselves. We expected to stay there merely until a table became available, but the wait staff presently observed that we were engrossed in our conversation, and left us alone for the whole afternoon—which suited us just fine.

      Kailee was dressed casually but attractively in a low-cut grey top, black fitted tights, tall black boots, and a beret that she referred to as her “lucky hat.” She carried a handbag so capacious that it was more luggage than purse.

Modelling for MXM, Spring 2007

      I told her my proposed itinerary for the interview: a chat about her modelling career, a specific discussion of some of her most memorable pictures, a few words about her life outside of modelling, some deeper questions, and finally a special “extra” section that I didn’t wish to elaborate on until later.

      We traded small talk as I organized my materials. I drew her attention to the big bay windows behind us, which bathed the café with light and opened a vista onto Central Park. “You can see why I thought that this would be a fine place to chat,” I told her.

      “Yeah, I love Central Park,” she responded. “I don’t come to Central Park often, but I wish I did.”

      “How safe is it these days?”

      “It’s perfectly safe during the day, but at night, I wouldn’t really go in the middle of Central Park, no,” she admitted.

      “Even in the post-Giuliani era?” I asked.

      “Yeah, not at night.”

      “By the way, I really appreciate this,” I mentioned. “This is very nice of you.” No words seemed adequate to express my gratitude to her for this marvellous opportunity. Kailee had been a source of fascination and mystery to her fans since the beginning of her career. At the time of our discussion (February 2009), she had never given a full-length interview to any publication, in any medium, and I was honoured to be the first.

      “Oh, thank you,” she replied casually. “You guys say a lot of positive things, and I just thought it would be a nice way to come in and…give my word.”

      I rummaged through my papers and pulled out my interview questions, as well as a recording device. I then produced a second recording device, which caused her to raise an eyebrow.

Modelling for MXM, Spring 2009

      “You see, I have no faith in technology,” I explained, “so I have—”

      “Two of them,” she finished for me.

      “In case one doesn’t do the job.”

      “You know, I don’t have any faith in technology anymore after today,” she related, “because every train that I’ve been on today has stalled, and stopped, and been late, and I’m kind of sick of technology. I have been for a while, but this is my final straw.”

      Again, I was struck by her professionalism. Instead of casually arriving for the interview whenever it suited her (as any girl as beautiful as Kailee was justified in doing), she had made a determined effort to be punctual—and what’s more, she was clearly accustomed to being on time for professional engagements.

      No wonder she is such a successful model, I thought. Clients can obviously depend on her.

      We then embarked on the interview proper, beginning with two preliminary questions.

      “Given some recent appalling developments in the plus-size industry, I have to ask you this, first and foremost: Would you ever betray the cause of size-celebration by appearing in a diet ad, a weight-loss TV show, or some other propaganda vehicle designed to make women feel bad about their appearance and to brainwash them into losing weight?”

      Kailee’s response was cautious. “Definitely I don’t agree with [names of diet companies],” she observed. ”And the food is disgusting.”

Modelling for MXM, Spring 2007

      I was pleased by her frank assessment. “This is good material,” I said with a smile.

      “No, I’m being serious,” she insisted. “The food is… Because when I was in high school, when I just started plus-size modelling, I… You kind of get self-conscious, because you’re starting out. I was really young—15, 17—and I thought, ‘Maybe I should trim down a little bit.’ And I tried [names of diet programs] and I was miserable. [AUDIO] Absolutely miserable. And—”

      At this point Kailee noticed the look of abject horror that had spread over my face as she had described her past weight concerns. I couldn’t believe that such a gorgeous young girl—who was curvy, yes, but at the smaller end of the plus spectrum—could ever have been brainwashed into wanting to diminish herself.

      “I know,” she said with a laugh, amused by my reaction. “But now I’ve come to my senses, and realized that dieting and me just don’t mix. And dieting and women should not mix. But, no, that’s how I realized the hard way that dieting is not the answer.”

      “Okay,” I replied uneasily.

      “No, no. I really don’t agree with dieting,” she repeated—and by the tone of her voice I knew that she meant it. “Every time a friend of mine goes on a diet or something, I go, ‘You’re not going to lose weight, and even if you do, it will come back. So don’t.’ But really, about eating healthy, [AUDIO] I believe that you should be able to eat whatever you want, but eat it slowly, and enjoy it, and relax about it, relax about food, because then it gives you a headache if you don’t relax about it.”

      I could hardly contain my delight at these words. To hear Kailee acknowledge that girls should eat whatever they want, and “relax” and “enjoy” food, was music to my ears. “I’m so happy to be interviewing you” I exclaimed, already star-struck, before asking my second preliminary question: “Would you ever betray the cause by diminishing yourself into a smaller size?”

Test photo

      Again, Kailee answered cautiously, carefully choosing her words. “I would never try and diet to get to a smaller size. I’m trying to just listen to what my body tells me, so whatever size comes from that, whatever natural size I am, I’m going to accept that.”

      It wasn’t quite the ironclad promise that I had hoped to hear, but it was still very encouraging. I returned to my previous theme and told her how much her fans hoped that she would never, ever sell out and appear in any campaigns for diet-starvation or exercise-torture companies, as some of her peers had done—prostituting themselves for dangerous drugs, for example.

      “Plus-size models have been given so much beauty,” I pointed out, “so to see one of them give that power, the power of their beauty, to the enemy—to a company whose sole purpose is to make women feel bad about themselves—is tragic, and the worst kind of betrayal.”

      “No, I agree,” she responded firmly. “I do not believe in diet pills.”

      “It’s almost like a Faustian bargain, isn’t it? You get a few pieces of silver, but you have to sell your soul.”

      “Yeah, I don’t think diet pills are a good thing at all,” she repeated.

      “Principle, or selling out,” I stated, defining the choice. “Helping improve girls’ body image, or selling out.”

      I didn’t want to belabour the point. I had made my pitch, and all that I could do was hope that she would take the words to heart.

* * *

      With the preliminaries out of the way, we moved on to a discussion of Kailee’s modelling career. The best way to delve into it, I thought, was to begin at the very beginning—with her first awareness of her own beauty. I asked her at what age she had realized that she was photogenic.

      “Hm. Photogenic?” she mused. “Well, when I was—”

      “Did people always tell you that you were pretty?” I elaborated, hoping that the modesty that I sensed in her wouldn’t inhibit her from answering the question.

Test photo

      “My mother always told me I was pretty,” she replied, smiling. “But, no, not always. You know, everyone goes through a kind of awkward phase in middle school and elementary school, and I definitely went through my awkward phase. But I thought I was super-photogenic when I was 3 and 4 and 5. And then when I hit 8th grade, 9th grade, 10th grade, I thought, ‘Oh my God, I don’t take good pictures.’ And then I guess my facial features balanced out. Because in middle school my brother went through the same thing. His nose grew bigger than his face, his eyes were smaller, and he just looked kind of awkward. And then all of a sudden his face kind of grew into itself, and now he looks very proportionate. And my face kind of did the same, so I started to be happier with the pictures that were coming out by the time I hit 10th grade, 11th grade—when, I would guess, I was 16; 15 or 16.”

      I found this transition from childhood confidence to teenage self-consciousness fascinating. Even princesses, I realized, are not immune to teen angst. And I thought about how adorable a young girl Kailee must have been in her avowedly “super-photogenic” childhood.

      “What prompted you to think of modelling?” I inquired. “Did you grow up dreaming of becoming a model?”

      “Well, truthfully, when I first walked into Ford I had no idea that there was a plus-size industry. What happened was—”

      “I obviously haven’t been doing my job,” I joked.

      Kailee chuckled. “Well, no, I mean, I just wasn’t aware of it. I was very aware of the whole modelling industry, and I was aware that there were maybe one or two plus-size models, but I didn’t know that there was a whole industry behind it, and so I never thought that could be me. But my mother, having super-confidence in me when I didn’t have confidence in myself—”

      “I’m starting to really like your mother,” I interjected, recalling how other curvaceous models, like Christina Schmidt, Kelsey Olson, and Whitney Thompson, had credited their mothers with bringing them up in positive environments.

Modelling for MXM, Fall 2006

      Kailee smiled. “Yeah, you would like my mother. [AUDIO] She was the one who kind of dragged me into the industry and said, ‘No, I know you can do this.’ And I said, ‘This is not fair, because I know that nothing’s going to happen. I’m just going to feel so stupid. And they’re just going to say no.’”

      The way in which Kailee relayed this experience made it very vivid. I could well imagine her sitting at Ford, pouting, disheartened, expecting the worst.

      “And then I just walked into the agency,” she continued. “And I was the second one in line. And the girl in front of me was 6 feet tall and really skinny. And I felt like it would never happen. But they stopped me: ‘Hold on right here. Wait right here.’ And then they brought someone else from the plus-size division, which was Gary Dakin at the time. And he asked, ‘How tall are you? How old are you?’ I didn’t know how tall I was. I didn’t know how much I weighed when he asked. So he said, ‘Come back in two days, and we’re going to talk.’ I thought, ‘Oh, this is just going to be a nice way of him saying, “No. Come back in two years,” and, “Lose weight and you’ll be a model.”’ But when I came back a couple of days later they signed me right on the spot. And then I saw the whole board of girls and realized, ‘There’s a plus-size industry. There’s plus-size models everywhere. That’s amazing!’ And that was really eye-opening. I mean, it was really cool to figure that out.”

      “What has been your favourite shoot to date, or your favourite photograph?” I asked.

      “Favourite shoot?” she echoed. “I have to think about that for a second. [AUDIO]Well, I love doing MXM shoots, because… Well, truthfully because their catering is amazing.”

''Gourmet'' magazine editorial, May 2009

      My eyes widened.

      “They’re good people,” she continued. “We all have so much fun at lunch. And even during shooting, they let me be creative in front of the camera. Instead of saying, ‘Only smile,’ or ‘Only look sad,’ they kind of just let me do what I want. But, you know, I just did a shoot for Gourmet Magazine, and we got to eat. Just simply eat. And they said, ‘Okay, just eat.’ It was two girls, and two guys, and they said, ‘Okay, just eat, and we’re going to shoot you.’” Kailee giggled. “It was amazing. And the food was…”

      I thought that I had died and gone to heaven. To learn that Kailee was so particularly pleased by the catering at MXM shoots was too wonderful to express. And then to hear her describe—with such relish—the pleasures of doing a shoot where she was encouraged to “just eat” was intoxicating. I realized that Kailee really had set aside the needless weight concerns of her youth, and had genuinely embraced her curvaceous appearance and natural appetite.

      The rapt look on my face prompted her to trail off.

      “I’m sorry,” I said. “Let me just savour the thought of that for a moment.”

      She laughed.

      “That’s good on so many levels,” I raved. “There’s a really positive message in that.”

      “Yeah, definitely,” she agreed, flashing her pearly whites.

      “Okay,” I said, venturing onto another topic. “Fans have always been fascinated by your changes of hair colour.”

      This too prompted a chuckle from her.

      “Why do you like to change it, from time to time?”

      “I’m indecisive,” she replied. “That’s really just it. I can’t decide. I just like to experiment and see which colour looks best on me, or whatever mood I’m in that day, or that month, or that year. But right now, I definitely… I wish I was naturally blonde, just because dyeing it blonde is kind of taxing on the hair. But I don’t know. Right now, I feel like I’m in my blonde phase, definitely.”

Modelling for MXM, Spring 2007

      “That was going to be my next question: What’s your favourite colour?”

      “Yeah. I like blonde best, because I feel more comfortable,” she stated. “But there are times when I’ll actually go red. ‘I’m going to go red!’ And then…”

      “And you have,” I reminded her. She had talked about going red with such roguishnes that it sounded like a transgression, like committing a delicious sin.

      “Yeah, I have. And then there’s the time I went really dark. My hair colour just relates to what I’m feeling at the time. It’s just me experimenting, figuring out what looks best, what feels best.”

      Turning to an issue of some importance, I pointed out to Kailee that from the very beginning of her career, fans had been delighted by the fact that she modelled at a very natural height: 5'6½. “Has your height ever been a challenge for you?” I asked.

      “Oh, yeah,” she replied with some dismay. “Absolutely. I’ve been turned down for jobs because they said I’m too short.”

      Dumbstruck by the foolishness of the industry, I could only emit a look of horror.

      She continued, without bitterness, but acknowledging the frustration of the situation. “And my agents say, ‘If you grow two or three inches, you’d be able to make a lot more money. You’d work a lot more.’ And I think, ‘Well, what do you want me to do about it?’ But when I was 5'6½ I was 15, when I was starting out. And I did grow 1 inch, 1½ inches maybe. But, yeah, I mean, I can’t do anything about my height. It is what it is.”

      “Do you believe that modelling should embrace girls with a more diverse range of heights?” I asked. There could only be one correct answer.

Modelling for MXM, Summer 2009

      “Yeah,” Kailee replied. “It’s mostly runway shows that are really, really strict about the height thing. For print ads, I think they’re a little bit more lenient, but I think also they can start to be a little bit more lenient. I think height shouldn’t be that big of a deal, as long as you have…”

      “Why do they put such a stress on height?” I interrupted her.

      “I guess it just goes along with the model stereotype, in a way,” Kailee opined. “People like that ‘wow’ factor. Especially for runway. I’ve done a little bit of runway here and there, but not any of the big plus-size-model shows because I am under their height preference.”

      “It’s just another example of the misguided application of the straight-size aesthetic to plus-size modelling,” I fumed. How could they not realize that the “wow” factor of Kailee’s superlative beauty would exceed any impression made by the mere height of a model?

      The industry’s prejudice was maddening, but I knew that while we could lament this one problem all afternoon, it would get us nowhere, so I moved on to another important issue.

      I conveyed to Kailee—who began her career as a size 12—how dearly fans had always wished that she might become a bit fuller-figured—and how delighted they were when she did. I asked her if she could appreciate why the size of the models who represent them is so important to many full-figured women, and why they vehemently reject faux-plus girls.

      “Because most women are a size 12 to 16,” Kailee noted. “I think that’s the majority of women. And faux plus-size models are just kind of in-between. They’re not straight-size and they’re not completely full-figured. [AUDIO] I think it gives women more hope and confidence when they see really full-figured women and girls in magazines, because they think, ‘Wow, if they can do that, they are able to kind of celebrate those bodies in the media, they maybe I don’t have to be so hard on myself about these 5, 10, 15, 20 pounds.’ Seeing fuller-figured celebrities has even given me confidence, because I think maybe Hollywood and the media is actually starting to be a little bit more accepting. It needs to happen.”

      It was an eloquent answer. Not for the first time in the interview, Kailee’s insight and intelligence deeply impressed me.

      “You’re also renowned for your fair complexion,” I commented, turning to a favourite topic. “Do you think that we might be seeing a renewed cultural appreciation for fair skin instead of the radioactive-tan look associated with Maxim magazine and the like?”

David's Prom magazine ad, 2006

      “Well, let me tell you a secret,” she began. “I went through that orange radioactive phase in my 10th grade. I thought self-tanner was the way to go. But I learned my lesson. I said ‘No. This looks bad in pictures. It looks bad in real life. It looks fake. It smells bad.’”

      This response shocked me even more than her previous admission of youthful self-consciousness had done. My heart broke to think of Kailee damaging that delicate, fair skin with the sun’s harmful rays, discolouring its fair perfection. But once again, she had drawn a sharp distinction between her past outlook and her present beliefs, and the vigour with which she now denounced tanning was most encouraging.

      “Definitely I agree that we need to have more natural-looking people in the spotlight,” she continued. “It just gives people more confidence to be natural, to be themselves. Like Scarlett Johanssen—she’s very fair. She has that kind of curvy and fair glow to her, and I really appreciate that. There are so many celebrities who put so much makeup on, and tanner, and hairstyling, and everything. But she’s very natural, and I notice that. She’s very fair and natural, and I think that’s a positive message. So, yeah, I definitely agree with less self-tanner, less super hair-spray, less makeup even, more natural.”

      “That’s another reason why I wanted to interview you here in the daylight, by the way,” I admitted. “So that I could see your fair features.” And it was true. The east side of the Petrie Court Café was one big glass wall which allowed the daylight to pour in, and in that natural illumination, Kailee’s fair complexion, with just a hint of pink flush at the cheeks, was dazzling.

      Kailee didn’t seem put off by my ulterior motive. I had the feeling that she was used to the adoring reactions of her fans.

      “From the beginning,” I ventured, “a particular aspect of your career that has thrilled the public has been your video work: first, your famous Ford promotional video—”

      “Yeah,” she said.

      “Do you know how often that keeps coming up, to this day?” I noted parenthetically.

Click to view

      “Really?” she replied. But I had a suspicion that she knew perfectly well what a hit that video had been.

      “—then your Ford 360 hairstyling video,” I continued, “then your David’s Bridal shoot; and, most recently, your Simply Be runway vids. How did you become so comfortable in front of the film camera?”

      “Well, I definitely wasn’t at the beginning, and I think people could tell that from the first video. They could tell that I wasn’t super-confident.”

      “But you were so good,” I emphasized.

      [AUDIO] “But I think what people liked about that is they saw that I was a little bit nervous. I was just kind of young and giggly and kind of, like, ‘Ooh!’” she breathed.

      “Yes, but that’s a good thing,” I insisted. I couldn’t abide anyone criticizing the sparkling masterpiece that was Kailee’s first video—not even the model who had created it.

      “Yeah. I mean, at the time I was so nervous,” she admitted. “That was when I just started out modelling, and I thought, ‘Oh my God. They’re going to do a video of me? What?’ So I guess without even trying, I came across as kind of natural, and people liked that. And, yeah, video… Well, I’m an aspiring actress, by the way, so I’m trying to be more comfortable in front of the camera. Because it’s not so easy. Maybe for some people it is, but for someone who’s shy naturally, it’s really not that easy. But the more I keep doing it, the better it gets.”

      I thought back to Barbara Brickner, who had similarly admitted that while shooting her first Mode editorial—in which she looked alluring and bold and sensual—she had actually been quite nervous. Perhaps Kailee was on to something—that a model’s nerves could, on occasion, work in her favour.

Screen capture from Kailee's first Ford video

      “By all accounts,” I told her, “that first Ford video was the best that was ever shot, compared to any other model’s.”


      “Everyone was amazed by the hair flip that you did,” I added, referring to the fans’ favourite moment.

      “Oh, yes,” she remembered. “Yeah, that was funny. I was going through a light-red-hair phase at the time.”

      I couldn’t resist showing her a screencap of the magical moment in her Ford video when she flips her hair back, and her tresses fly all around her head in the most enchanting manner.

      “Where did you get the idea to do that?” I inquired. “Did that just spontaneously happen?”

      “They said they wanted to see the side of me, but without my hair in the way. But I’ve always had this tumultuous relationship with my hair, so I just thought… That was what I did a lot when I was younger. It just happened. Just happened.”

      It was like asking a composer how he had created the motif for a great symphony. It wasn’t a conscious action; it was the unerring instinct of talent. “If you want to do that during your shoots, please feel free,” I encouraged her, “because it’s a winning move.”

      “Okay,” she responded with a laugh. “I’ll keep that in mind.”

      I mentioned to Kailee how smoothly and gracefully she moved in her videos, particularly in her David’s Prom clips, in which she performed such elegant turns in her prom gowns, and asked her if she had ever studied dance.

Screen capture from one of Kailee's videos for David's Prom 2008

      “No. Never,” she responded.

      “No ballet?”

      “In fact,” she said, “I was just… I was watching… What was I watching the other day? It was something about dancing, and I thought, wow, I could never be a dancer. It’s just not me. I never had that passion for dancing.”

      I was surprised, because dance was something that I had always associated with plus-size models. Many of Kailee’s peers had expressed a love of dance, or had demonstrated their dancing prowess in images and videos. It had something to do with their extreme physicality, with their sweet surrender to their bodies’ inclinations. But Kailee was different in this regard (at least in terms of her self-assessment; in practice, her movements were smoother and more beautiful than those of almost any other currently working model).

      “I don’t know,” she mused. “I’ve always wanted to do acting, and performing too, so you kind of have to be comfortable with your body—or at least pretend to be if you’re not—so, yeah, I just had to try and do it flowing and naturally. That’s what they liked, so…”

      “You did it so gracefully,” I enthused. “Poetry in motion.”

      “Thank you.”

      “Now we can discuss your Simply Be videos. Fans have always loved your ‘Look-at-me-I’m-so-gorgeous-and-don’t-you-know-it’ expressions.”

      Kailee laughed. She was tickled by the description.

      “They have. They really have,” I affirmed. “What goes through your mind when you perform in your videos, and particularly when you flash those thrilling looks?”

Click to view

      “Well, that’s definitely not how I walk down the street in everyday life,” she admitted.


      “No. Unfortunately no.”

      “You would stop traffic.”

      “But when you’re in front of the camera and they want you to work it, you’ve just got to bring it,” she explained. “You’ve got to deliver, and you’ve got to give them what they want. So that’s really what’s going through my mind: Walk that confident strut. Give ’em what they want.”

      “Well, your movements in those Simple Be videos are utterly amazing,” I pointed out. “Imagine: twenty solid minutes of Kailee O’Sullivan.”

      “Yeah, that shoot was… I was in London for two weeks, actually, but that shoot was pretty gruelling. I did so many outfits.”

      And yet she had managed to do each video differently, I told her, which was a modelling tour de force.

      “Yeah, I had fun with that shoot. It was a lot of fun trying on all the clothes, and walking. It was fun doing that confident catwalk. It was fun.”

Unpublished ''Modern Bride'' magazine editorial

      I wanted to press her on her exciting vanity, though. “Why do you think fans respond so enthusiastically to that particular demeanour of yours—that long phrase that I just gave you: ‘Look-at-me-I’m-so-gorgeous-and-don’t-you-know-it’?”

      [AUDIO] “It’s that confidence,” she reasoned. “That’s what I think most people respond to, is confidence, and that kind of look, that look when you gaze into the camera like that.”

      At this point Kailee unconsciously flashed one of her thrilling, vain glances right in front of me. It was a heart-stopping moment.

      “You just did it, right there.”

      “Oh, did I?” she asked innocently. “See, I don’t even realize… Maybe I do do it in everyday life!”

      I laughed, but I enjoyed her suggestion. Very much.

      “But I guess people respond to confidence,” she continued, “and that look definitely represents a confident woman. I know I respond to confidence. I gravitate towards people who are confident, because when I was younger, as you can probably tell by now, I wasn’t confident. I wasn’t as confident as I’ve grown to be. And it took time.”

      “Has plus-size modelling helped you in that?” I asked.

      “At first, it hindered me, and then it really helped,” she revealed, “because even though it is plus-size modelling, there still is an ideal body type that clients sort of look for.”

      I flinched inwardly at this statement, since it touched on the lingering frustration that the public has always had with the narrow size standards of the plus-size industry. But not wanting to get diverted, I simply mentioned, “You’ll notice that the general public, and Judgment of Paris readers, prefer a very different ideal.”

Unpublished ''Modern Bride'' magazine editorial

      “Yeah. Yeah, yeah, definitely,” she acknowledged.

      I had been growing terribly thirsty during our conversation, so I asked Kailee—who was facing in the direction of the bartender—to flag him down the next time she saw him. She did, whereupon I ordered a mineral water (figuring that it was incumbent on us to purchase something), while she ordered a glass of ordinary water.

      Presently the waiter brought a bottle of mineral water, as well as a glass containing what I assumed was Kailee’s beverage. Offering a toast, I clinked my bottle to her glass, and we drank to “a better ideal.”

      At that point, the bartender came along with a second glass of water.

      I was puzzled by this, until I realized that the first glass had actually contained my mineral water. The bottle had merely held the extra. (And readers, if this sounds confusing to you, imagine my own bewilderment at the time.)

      Seeing my embarrassment, Kailee graciously said that she would accept the mineral water that she was drinking, and asked that a second be brought. She was polite enough not to laugh at my befuddlement.

      “See? You’re distracting me,” I scolded her. “I can’t concentrate.”

      “Sorry about that,” she responded with some amusement.

      “I’m sure you have that effect on many men,” I speculated, and proceeded with the interview.

Modelling for Rubie's, Hallowe'en 2008

      “You recently did a fun shoot promoting Hallowe’en costumes, but you didn’t load it with irony, or ham it up. Instead, you did it with great sincerity. You were alluring, or funny, as the costumes required. How did you like that experience? Did you feel like, ‘What am I doing here?’ Or did you enjoy it as something different?”

      [AUDIO] “It was definitely different,” she recounted. “And the people that were there were totally fun and kind of goofy and fun to work with. I kind of just had to get into the role and the character of whatever costume I was in. So a lot of it was ‘sexy cavewoman,’ ‘sexy maid,’ or nurse, or whatever. But I had to get into that role, and they would just say, ‘Work it,’ ‘Give it what you got.’ So that’s basically the story behind that. It was a lot of fun, though. For example, I did a clown costume, and it wasn’t a sexy clown costume, it was a goofy clown costume, so I had to do a goofy expression, a goofy face. And I did. It was fun.”

      I was still eager to hear some self-adoration from Kailee, so I gave her a leading question.

      “Do you ever have moments when you look at one of your pictures and think, ‘Wow, I look good’?”

      “Yeah, I do,” she replied, but quickly added, “And I also have moments when I think, ‘Ooh, that is not a very flattering picture.’ But, yeah, it waxes and wanes. It balances out each other. And more recently, I’ve been liking my pictures that are coming out. Definitely. Because I think I’ve finally gotten my hair the colour that I want, and…”

      I told her that it had looked good in every incarnation.

      “To what exotic locations have you travelled in your modelling career?” I asked next.

      “Hmm. Exotic? Well, the first…”

Modelling for Laura Prom, 2006

      “Anywhere outside North America is exotic to Canadians,” I added.

      “Right, right,” she acknowledged. “The first place that I travelled for any shoot was Bermuda for the Laura Prom campaign.”

      “Oh, really?”

      “Yeah, that was in Bermuda. And I was 15, so I took my mother and my aunt with me, because that was my first… And so that was really fun. But I don’t know. Exotic? I haven’t been able to go to any truly exotic places yet, but I’ve been to Germany. I’ve been to London. I went to Paris and Italy, but that was after I did my shoot in London. I said, ‘I’m going to go backpacking around Europe.’”

      “You did that?” I asked, thoroughly impressed.


      “For how long?”

      “For a month.”

      “Isn’t that the best experience?” I rhapsodized, recalling my own European travels.

      “Oh, it was great. It was great. I went by myself, and I was couch surfing. It felt really good to be sort of just free from everyone.”

      By herself? Good heavens, a girl still in her teens backpacking solo across Europe? I could hardly believe it. I considered Kailee incredibly brave, and told her so.

Modelling for Sodrap, Spring/Summer 2009

      [AUDIO] “See, everyone told me I was brave, but I just thought, ‘No, I have to do this. I want to travel. I want to go everywhere.’ I was going to originally go with my friend, but she sort of backed out at the last minute. She said, ‘No, I can’t afford it.’ I thought, ‘Urrr. I don’t care. I’m going by myself.’ So I went to London. Actually, you know what? I signed with an agency in London [i.e., Hughes Models], and right away they sent me on a job to Barcelona. And that was cool, but I barely got to see Barcelona at all. It was only for a day, and I didn’t really see much at all. And then they sent me to Copenhagen. So I went to those two places just for a day, the time in-between. But then I went to Paris, and then five different cities in Italy, and that was a lot of fun. I’ve been to California a lot for work. And Montreal. That’s pretty much it.”

      At that moment I remembered that I had informed Kailee that the interview would take approximately one hour. It was already time to turn over the tape in the voice recorder, and 4 o’clock was approaching fast. With some trepidation, I asked her how much time she had, and if she genuinely needed to depart at 4.

      Imagine my delight when she responded, “No. Actually, I have an appointment at 7, so…”

      Splendid! Even if she had to leave by 6, this meant that I had two more hours of her time. Once again I noted how gracious she was, and how generous.

      I continued on the European tack.

      “Your Facebook page has a picture of you in Paris, in front of Notre Dame. How did you like Paris? What stood out to you?”

Modelling for Fashion Bug, Winter 2007

      “Oh, it was so nice,” she recollected.

      “Did you see the Catacombs?”

      “Um…I might have.”

      “You would remember if you had. They run underneath the city, a mile’s length of skulls embedded in the walls.”

      “Oh, no, then I definitely did not.”

      “You’ll have to go back,” I said, grinning.

      “Yeah. I was originally supposed to be in Paris for a week, or a little bit more than a week,” she remembered, “and then because I got a job in Barcelona it took two days from Paris, and then I had to also fly back to London for a day, so I was only there for three and a half days.”

      “But you saw the Louvre…” I prompted her.

      “Yeah, I saw the Louvre, and I met a lot of great people,” she related. “They were really friendly. There’s that assumption that French people are not friendly, but to me they were just so friendly. [AUDIO] And the food was great, and the people were fun to meet. The friends that I met there, we went out to one of the bridges and just sat and drank wine and ate cheese and watched the sunset. And it was just so…like it was from a movie. I had such a great time. It was so European, the way people were.”

      “It’s redundant to speak of ‘sights’ in Paris,” I gushed. “The whole city is a sight.”

Modelling for MXM, Fall 2007

      “Oh, absolutely. The architecture, the buildings. Yeah, you’re right, everything there is definitely a sight. Something to look at, and gaze at. It’s fascinating. And the people there… It would have been great even if I had met nobody. It would have been beautiful. But the people made it so much more amazing for me; when I met the right people, and just made friends, and socialized. It was just great.”

      “As for the Parisians being polite and friendly,” I commented cynically, “I think it helps, as in your case, to be a pretty girl, because that’s not the experience that most people have.”

      “Oh, I definitely did meet some rude Parisians, men and women.” she acknowledged. “But for the most part I took away a very positive experience from people.”

      I couldn’t help but reflect on the differences in our approaches to travel. For me, the locals were simply obstacles to my picture-taking. But Kailee seemed genuinely to appreciate people, to enjoy meeting them. Such geniality can be a great asset to a model.

      “Parlez-vous français?”

      “Un très petit peut,” she responded, with a flawless French accent that belied her modest response.

      “It’s enough,” I said. “Just that little bit helps so much.”

      “Actually, I was studying French for a little bit before I went, and just the little bit I knew helped me get around,” she mentioned. “It really saved me.”

      “And you pick it up so quickly when you’re there, immersed in the culture.”

Modelling for MXM, Summer 2009

      “Right. Absolutely.”

      “Sprechen Sie Deutsch?” I ventured, but here my luck ran out.

      “No,” she replied. Then added, “Nein,” with a laugh.

      “But you did do a shoot for the Otto catalogue,” I reminded her.

      “Yeah. That was fun. I loved working with them so much, but I think they were bought out by another company,” she stated. “That’s what everyone told me, that they were kind of merging companies somehow, so they had to use a whole different marketing plan, or something like that.”

      “What would be your ideal photoshoot, in terms of setting, theme, what you would be wearing?” I was curious as to where her creative inclinations would take her.

      “Mmm. Probably India, or Indonesia,” she reflected. “Somewhere in the Far East. I love nature, and I just feel like… I just did a shoot with MXM. The whole theme was ‘hippie,’ and that was right up my alley. It was just so me, the clothes and the feeling, the vibe. I just love it. So anything kind of earthy, natural. I love Eastern everything: food, decor, belief system. It’s all fascinating to me. I love it.”

      “That’s the campaign that’s out there now, right?” I asked, erroneously. “All of the images have been cropped to your face.”

      “Oh, really?”

      “They obviously like you. The MXM approach almost seems to be, ‘Forget about the clothes we’re selling. Just look at her,’” I said, approvingly.

Modelling for Anna Scholz, Spring/Summer 2009

      “I’ve seen the ones from the rock ’n’ roll shoot…”

      “There’s one after that?”

      “Yeah. I was just in Florida shooting in Miami,” she informed me.

      “Oh, so this will be the summer promotion. Something for us to look forward to.” But I didn’t realize at the time just how beautiful this campaign would prove to be.

      “Yeah, yeah, yeah. I just came back two weeks ago,” she noted.

      “What other exciting campaigns are in the works? What about Anna Scholz?”

      “Yeah, I did do a shoot with her,” she confirmed. “That was a lot of fun. I love them. It should be coming out—”

      “Because fans saw a few pictures from that nearly half a year ago…”

      “I shot that just over the summer, and they said that it was going to be the campaign coming up,” she mentioned. “They were saying they want to fly me back, but with the economy, everybody’s cutting every budget. It’s not good.”

* * *

      I now wanted to try an experiment with Kailee. I asked her if it would be all right if I showed her a series of her most famous photographs, and recorded her reactions.

      She readily agreed, and even seemed intrigued by the idea.

      First, I presented an image from her celebrated Laura Prom promotion, one of the earliest campaigns in which Judgment of Paris readers had noticed her. I told Kailee that with her blonde hair and spun-sugar complexion, this picture showed her in her “princess identity.”

Modelling for Laura Prom 2006

      “That was… I was 15,” she reminisced.

      “This picture gave you your first gallery at The Judgment of Paris,” I told her.

      “Oh, yeah?”

      “Yes. As soon as it came out, fans determined that ‘She has to have a gallery.’”

      “Oh, wow.”

      I could tell that she was still getting used to the idea of scrutinizing her own work, so I asked her, “Can you, in fact, look at your pictures and imagine what someone else might be seeing when they look at them?”

      “That’s hard, actually,” she admitted.

      “Here, for example, you resemble a storybook princess from another time. The picture does have that quality, doesn’t it?”

      [AUDIO] “Yeah, definitely,” she agreed. “But, you know what? It’s really hard to kind of look outside yourself and say, ‘Oh, well, I was doing this at that moment, and I felt that, and I was…’ But, yeah, I guess I can see… Yeah, I do look kind of princess-like, very fairy-tale. But I also think I look young there. I was young. That was a long time ago.”

      I was delighted to hear Kailee call herself “princess like.” But I was equally struck by how she referred to her youth as if it were part of a past era, something that had occurred ages ago.

      I told her, “You still look very young,” to which she replied, “That’s good.” But I realized how consciously Kailee thought of herself as being older and more mature than she was in her high-school days, recent though they may have been.

Editorial page in ''Glamour'' magazine, May 2007

      Next we moved on to an image to which I was particularly eager to hear Kailee’s reaction.

      “This famous Glamour tear sheet caused an absolute sensation,” I reminded her. “All of your fans loved it, and it spread your fame far and wide. Why do you think people responded to it so enthusiastically?”

      “Because it’s unapologetic,” she proposed. “It’s out there. And I was feeling really confident, that day especially, and everyone was really encouraging, and everyone was just really happy with that. And I definitely think it is a positive message to send out to girls around the world. Because I did read some of the comments, the things that people wrote about it at the time.”

      “But I did not think it was going to cause any sort of sensation,” she continued. “I was unaware, when I went on the casting for this particular shoot. They didn’t photograph me in black underwear. I think I was wearing this hat, (this is my lucky hat,) and I was wearing a black shirt. They just photographed me in that. They just said, ‘That’s fine. You look great how you are.’ I was unaware that it was a bra-and-underwear shoot. And then they said, ‘We’re going to shoot you next week, and it’s going to be lingerie.’ I thought, ‘Oh. Okay.’ So I just kind of… I was nervous, because it was the first one I had done, but I thought, ‘They obviously like me for what I looked like, so I can’t try and, you know, “get in shape” for the shoot.’ But, yeah, I think it was definitely a positive image. A lot of girls were really surprisingly grateful. I didn’t expect that. But they were really happy with that, because…” She trailed off.

      “I think you can understand why it was such a hit,” I prompted her. “Usually, even when plus-size models are shown in unmentionables, the look is alien to most women. The models practically look straight size, and have ‘toned’ figures. It’s still an artificial appearance.”

      “Yeah, definitely. A lot of the girls have beautiful bodies,” she was quick to stipulate, “but a lot of them are thinner. And I think I’m definitely in the bigger size, so people were… I can understand now. I just didn’t see it coming when it happened. And now I’m happy about it. Definitely.”

      I then pulled out an image from her very first MXM campaign, one which showed her in the protective embrace of a male model.

Modelling for MXM, Fall 2006

      “Each of these pictures caused a minor riot when it came out,” I recounted.

      “Oh, really?”

      “What’s interesting about this picture,” I observed, “is the vulnerability in your eyes. And yet you’re engaging the viewer. You’re melting in his arms, but you’re not completely helpless.”

      “Well, I think at that moment, I was… I think that was the first shoot I did with a male model where it was that intimate, and that close, so I definitely was vulnerable at that moment. You can’t help it, you know what I mean? I’m sure any male model would say the same for any other female model.”

      “Yes, I’m sure he was having a heart attack,” I affirmed.

      She laughed. “But when you have to do that in front of the camera, we say, ‘All right, well, we have to kind of get rid of those preconceived notions, or any kind of nerves and insecurities.’ So, yeah, I was definitely vulnerable in that moment, so I guess it came across.”

      “But this is one of your signature looks. You’ve repeated it on numerous occasions.”

      “I don’t think I was aware of it,” she commented.


      “It really works. If there’s a look that Kailee O’Sullivan does that no other plus-size model does as well, that’s probably it. Incidentally, did you by any chance watch Cycle 10 of America’s Next Top Model?”

      “I don’t watch reality shows,” she replied, and I was secretly delighted. A model who prefers museum visits to reality television? It gave me hope for modern society.

      “Well, a plus-size model won that cycle—”

      “Yes, I did hear that,” she jumped in. “You know what? I was very happy about that. When I heard, I was really happy about that, because I didn’t think that would ever happen. I think when that show first came out, I might have watched one or two episodes, but I’m not into reality shows at all.”

      “Anyway, the winner of the cycle, for her second-to-last shoot, did a photo that was a near-duplicate of this one,” I explained, “and I think it was designed that way.”



      Next I pulled out a particularly celebrated test photograph, a masterpiece of feminine sensuality, and introduced it as one of her most famous images.

Test photo

      “Really?” she said with affected surprise. I had a feeling that she knew just how popular this picture was.

      “It’s been cited several times as the ideal plus-size-model test photo. Why is this such a perfect image?” I asked rhetorically. “It shows you full-figured. It shows you fair-featured. The dress is body-conscious. It’s revealing, but it’s modest at the same time, and the backdrop is a natural setting. How often do you see shoots set against a bare, white screen—”

      “Right,” she acknowledged.

      “—or in a dark alley, or something like that?” I continued. “Don’t you find that there’s something special about presenting a model in a natural location instead?”


      “And the beauty of the model harmonizes with the beauty of the setting.”

      “Yeah. Like I was saying before, I love nature, and I love being in nature.”

      That reminded me to ask her where the photograph had been taken.

      “This was shot, going on three years ago now, in Battery Park,” she told me.

      I was astonished. “Battery Park? Here in New York?”


      “This is in New York? Wow. So there is beauty to be found in the midst of—”

      [AUDIO] “It’s a very, very small park,” she recollected, “but it was really, really lovely there on the water. Oh, it was such a beautiful summer day. I remember it really vividly. It was a beautiful, beautiful, hot summer day, and we were right on the water, and the sun was setting, and it made me be in such a good mood.”

      “Yes,” I sighed, drinking it all in. She was describing paradise on earth.

Test photo

      “And that came across in the picture.”

      “Idyllic,” I concurred. “A slice of heaven.”

      Kailee laughed, but it was true.

      I wanted to inquire about at least one more test photo, one of the most dramatic images that any plus-size model had ever created—her famous “Solitary Reaper” picture. I asked if it had been taken in a bona fide wheatfield.

      “That was actually at my house on Long Island.”

      “This was a real wheatfield?” I asked, pleasantly surprised. “This wasn’t created in a studio, with Photoshop?” That had always been my suspicion, because its beauty, its perfection, seemed too wondrous to be authentic.

      “No, no. That was—”

      “This is the real thing?”

      “But, no. It wasn’t even a wheat field. Everyone asks me if it’s in Oklahoma.”

      “Sure,” I said. I had certainly thought so.

      “They go, ‘Did you go to Oklahoma?’ And I say, no,” she explained. “That is a nature preserve right near my house in Long Island, and it’s just really, really beautiful. It’s natural. Yeah, there was just wheat shooting up everywhere. I don’t even know if it’s wheat.”

      “But look at your expression. Is that dramatic, or what?”


      “Isn’t that epic? With the sky…”

      “Yes, I thought the background was fantastic,” she said, seizing upon my reference to the setting, but dodging my compliment about her pose. Miss O’Sullivan’s modesty is one of her classiest traits, but I was eager to hear Kailee give herself the praise that she deserved.

Modelling for MXM, Winter 2006

      “Oh, come on. Say it,” I encouraged her. “You’re fantastic in this too.”

      [AUDIO] “Well, you know, I do. I think I look good in that picture. I mean I look pretty… What’s the word? Let’s see. It looks like an epic movie, where the woman is… The heroine is standing in the background. I was just kind of gazing out into nature, so it was a natural expression. It wasn’t like a forced thing.”

      “When this was posted on the forum,” I told her, ”someone appended a Wordsworth poem to it. They were so inspired.”

      Having heard Kailee acknowledge her beauty in that phenomenal image, I wondered what she would say about her appearance in an even more overtly seductive photo. I mentioned how the outfit must have drawn out her more alluring tendencies.

      “That was another MXM shoot,” she noted, “and it was just kind of… It had to be very sensual. It was a Christmas campaign, I remember. So it was just kind of sensual, and natural, and kind of sexy. I had to portray that.”

      “It would work for Valentine’s Day too,” I said, thinking of the day on which this interview was being conducted.

      “Yeah, it does work for Valentine’s Day,” she concurred.

      Next, I turned to a photograph from another one of her most celebrated campaigns, an image that fans particularly appreciated because it showed Kailee in an indolent, recumbent state.

      “Everyone loved this picture,” I told her. “This was for Maurice’s. Once again, the natural setting harmonizes with—”

      “Yeah, that was in Miami,” she identified. “It was a fun shoot. But I got pretty badly sunburned that day. Really bad.”

Modelling for Maurice's, Summer 2007

      “Well, fortunately the picture was taken before your burn appeared, so it still showed your fair skin. And do you know what’s beautiful about your figure here? It’s soft. It’s not toned. Please, above all else,” I exhorted, “please stay away from the gym.”

      She laughed.

      “The gym is the destroyer of plus-size models,” I cautioned her. “The public avidly responds to models with softer figures. A model with a more natural physique seems more approachable than a model whose figure looks like it’s been…pilatecized.”

      “Yeah, definitely,” she agreed.

      And now we came to what is perhaps Kailee’s darkest, most passionate, most mysterious image—mysterious because of its content, and mysterious because no one hitherto knew its source.

      “This was a test?” I asked.

      “This was not a test shot, actually.”

      “This was not a test shot?”

      “No. Um, it was an editorial—”

      “My God,” I gasped, already preparing to track down the publication as soon as the interview was over.

      “—for Modern Bride magazine that never got published.”

      “Never got published?” I echoed in bewilderment.

      “It never came out. I don’t know why. I was looking forward to it. But yeah, I love, love, love those pictures. I love them. Because I feel—”

Unpublished editorial for ''Modern Bride''' magazine

      “This one above all. They’re all beautiful, but this one seized the collective imagination.”

      “Thank you,” she replied. “When you’re looking at you, it’s so hard to look at pictures from an unbiased or objective—”

      “You can be biased,” I grinned.

      “But, no, I looked at it, and I thought, ‘Okay, you know what?” she divulged. “That’s a good picture. I like that picture.’”

      Again, it was so wonderful to hear her praise her own work. “See, unlike the gentle expressions that you sometimes adopt,” I observed, “there’s a cruelty to your look here, if you know what I’m getting at.”

      “Yeah,” she laughed.

      “In an Evil Princess kind of way?” I said, growing more intense.

      “Yeah, definitely. Like I said, I had to get into that role.”

      “If this is a bridal editorial,” I fantasized, “then this image says, ‘Okay, you’ve married me. You’re going to be my slave for all time.’”

      “Wow, you know what?” she said, not quite ready to go that far. “That wasn’t going through my mind at the time, but… What was I thinking?”

      “Yes, what goes through your mind in order to generate such a look?”

      “I just had to feel the dress, feel the hair, feel the makeup,” she explained. “The apartment that we shot in was really glamorous, and I had to get into character, really feel it, get vampy, and… You’ve just got to feel it. You’ve got to feel what you’re in.”


      “You did a great job.”

      “Thank you.”

      I was thrilled to hear Kailee give herself the praise that she deserved, yet I was conscious that I was taking up a great deal of time with this exercise. “Almost done,” I told her, hoping that I wasn’t testing her patience. But her enthusiastic response allayed my fears.

      “No, I’m enjoying this,” she said, unexpectedly and quite sincerely.

      “You are?”

      “Yeah, absolutely.”

      “You’re just saying that to be nice.”

      “No, I swear I am,” she reassured me. “I don’t know. It’s just fun to kind of give my point of view and talk about… I mean, this is summing up my whole past five years. It’s interesting. And you know what? I enjoy kind of giving my input on the industry, and I feel like it’s so important to express that people need to be accepting of natural bodies. Organic, you know?”

      “I’m having a good time too,” I blurted out, adding, “I guess you can’t tell,” laughing at how obvious I probably was.

Modelling for David's Prom 2008

      “Well, thank you.”

      I was curious to hear what she would say about the next image, a picture from her David’s Prom campaign, which showed her looking very buxom, yet innocent.

      “This photograph is a complete contrast from the previous one. Again you’re in a splendid, feminine gown, but here you look doll-like, gentle, and soft rather than ‘fierce.’ Do you see that?” I asked her “One often hears the word ‘fierce’ stipulated as a modelling prerequisite, but don’t you think that there’s a place for something like this, a gentler look?”

      “Yeah, absolutely,” she agreed. “I love those words, ‘soft’ and ‘feminine.’”

      “Particularly suitable for a plus-size model?” I queried, hoping to pry her out of her diplomatic stance on sizes, and into plus-favouritism.

      “Yeah, I mean, that’s what I’m all about, is—”

      “Something that a plus-size model can do better than a straight-size waif can?”

      She chuckled. “Um, I can’t say something like that.”


      “I don’t want to be too bitchy,” she uttered, biting off the last word in a seductively wicked way.

      “Fans like bitchy,” I said quietly.

      “When it comes to being soft and feminine, you think of curves and flesh, so, I mean, it is what it is. I’m not just talking about myself. I’m saying—”

      “You can be talking about yourself,” I murmured.

      [AUDIO] “I think that plus-size women, they’re beautiful because they are very feminine,” she asserted. “And that’s something I’ve been very interested in lately. Not so much my whole career. Lately I’ve been very interested in the portrayal of women in the media, and society even, realizing that women are feminine by nature. We need to represent that instead of shunning that, and shunning curves and flesh and, you know, in the media.”

      “If I had made all this up,” I said in awe, “I couldn’t have written your lines any better.”

Modelling for MXM, Winter 2008

      Kailee laughed at that, but it was true. While she was being careful to note her appreciation for all body types, she was also praising the properties of full-figured bodies that made them uniquely attractive, enthusing about “flesh” in a way that seemed daring—especially to me, since I had always been cautious about using that potent word. Flesh. It seemed such a decadent expression, with transgressive implications.

      But how I wished I’d had a video camera to capture Kailee’s “I don’t want to sound too bitchy” comment. Although her gentler demeanour is her default nature, I could perceive the dollop of darkness that enabled her to create her “evil princess” image for Modern Bride. Kailee had layers upon layers to her personalty, I realized, and was boundlessly complex and multi-faceted.

      Now I turned to a more recent, very sinuous MXM image.

      “What makes this picture so wonderful?” I asked rhetorically. “Notice the S-curve of the body. How often do you hear, in the fashion industry, an insistence on angles. ‘Oh, she has great angles.’ ‘Oh, she’s got a great bony figure; she’s jutting out one elbow in this direction, and one elbow in this direction.’ But this is not about angles at all. This is about a soft, curvy shape.”

      “Right, right.”

      “Isn’t there a place for this, in the fashion industry?”

      “Like I said, I love curvy, feminine women,” Kailee avowed. “That’s beautiful. But, yeah, angles are definitely a big thing. When it comes to pictures, especially for straight-size models, people love those angles. But when it comes to bodies, I think for plus-size women, it’s definitely curves. It’s beautiful.”

      “Notice the business with the hair. You appear to be ready to do that amazing hair flip from your Ford video.”

      She laughed.

      My final offering was a picture from the then-current MXM promotion, the Spring 2009 campaign.

      “Okay, here’s the last one for today, and the most recent. Look at those eyes. They just leap off the page. How do you make your eyes pop like that?”

      “Well, I have to say that it’s due in part to the makeup,” she conceded. “They used the right colouring, the right shadow, this and that.”

Modelling for MXM, Spring 2009

      “Okay,” I noted.

      “But you know, you’ve got to have expression in your eyes,” she added. “That’s a huge part of modelling. And you just have to open your eyes wide. Sometimes you have to look surprised, even. That just opens your eyes. Yeah, a lot of that is because of makeup. But when you have the right makeup, you have to work that makeup. You can’t just let it sit on you and be, like…”

      She demonstrated a hilarious dead-eyed expression.

      “You’ve got to show it,” she continued. “You’ve got to show that you own that makeup, you own that outfit, you own that hair.”

      “Are you wearing lip colour now?” I asked. Her lips looked so natural that I honestly couldn’t tell if she was made up or not.

      “Yeah, I’m wearing a lip stain, a lip tint. That’s really the only makeup I cannot live without. I call it my lip tint. I don’t wear a lot of eye makeup, but I like lips,” she said, in an unintentionally flirtatious way.

      “It’s an amazing shade on you,” I observed.


      “On the forum, fans have said that the one colour that’s even more attractive than dark-red lips are baby-pink lips.”

      “Yeah. More natural, I believe,” she pointed out. “But I do love red lipstick. It’s simple and it’s classic. If you want to get dressed up, it’s the simplest thing you can do to make a dramatic effect.”

      My intent had been to hold off on the weightier questions until later in the discussion, but I wanted to use one final modelling-related query as a segué into the next section of the interview, which would explore Kailee’s personality and character.

      “How do you feel about the idea of young girls looking up to you as a role model for positive body image—that your images can help them embrace their natural body shape rather than starving themselves?”

Modelling for Anna Scholz, Spring/Summer 2009

      Her response impressed me greatly.

      “It’s a responsibility that I never expected I would have. It never occurred to me that this could happen. But, yeah, I feel the responsibility, definitely.

      “But I feel like it’s important [AUDIO] to send the message to embrace your natural body, and to enjoy food,” she continued. “I think that’s so important: to enjoy food. Because in America especially, the relationship with food, it’s just so… It’s unbalanced. I could see that definitely when I went to Europe and travelled. I mean, food there is a part of life. They don’t shun it. They don’t talk about diets. It’s not in their vocabulary. The word ‘diet’ is not in their vocabulary. It’s not in their mind. So I think more important than anything is to give a message to accept your body, or embrace your body, live healthfully, enjoy food, eat what you want, and everything needs to be balanced.”

      I was enraptured to hear these sentiments from Kailee. She stated them with great conviction; not hesitantly, but with the determination of a personal philosophy, one that she had developed for herself.

      Her European travels, intersecting with her career as a plus-size model, had clearly given her a unique perspective. How many girls of her age appreciated traditional Western culture or Classical aesthetic ideals? Thanks to her exposure to both of these unmodern influences, Kailee saw the world from a vantage point that few of her peers possessed.

      I realized then and there how singular she was, and what an extraordinary role model she could be for today’s youth. The second half of our conversation, which turned from Kailee the model to Kailee the person, only strengthened this impression, for the richness of Miss O’Sullivan’s character—as I was about to discover—is every bit as captivating as her personal beauty.

(Continue to Part II.)

Kailee O’Sullivan Galleries: One · Two · Three

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