Being the toast of the town is an inherently transitory title, but Connie Fleming has spent the last four decades proving that once an It-girl, forever an It-girl. The supermodel first made a name for herself in the ’80s as the muse to designers like Thierry Mugler , Vivienne Westwood , and Jean Paul Gaultier , starring in some of the most iconic and reshared fashion images of all-time and blazing a path as one of the first Black trans models in the industry. But Fleming’s legendary lore doesn’t end there. She went on to become an in-demand fashion illustrator, beloved downtown fixture as the door girl at Le Bain, and recently returned to modeling, walking the runway as well as starring in Burberry’s new 170th anniversary campaign. The brand’s photo series captures creatives across four global cities showing off how they style the brand’s iconic pieces of outerwear. To mark this moment, Fleming called us to chat about how to stay chic while bundling up for winter, dancing like nobody’s watching, and what it means to be a living icon.
KIRKPATRICK: Thank you so much for doing this. I wanted to start with the Burberry campaign you just participated in. Do you have a personal relationship to the brand?
FLEMING: A personal relationship, no. Just admiring the classic trench and the history that makes it such a style touchstone. There’s also the golden age of Hollywood, that English film history, Sherlock Holmes and Miss Marple. Also, there’s that depression when it’s a rainy day, but if you have a good pair of wellies and a great trench raincoat, it lifts you.
KIRKPATRICK: Definitely. I like that there is a timelessness to all these pieces. And like you said, an outfit really can be so transformative of your mood or the type of day you’re going to have. It changes how you feel about yourself.
FLEMING: It’s childlike, jumping in puddles, that sort of thing.
KIRKPATRICK: Because the campaign is all about outerwear, do you have any tips for staying fashionable when you are all bundled up? Because I get into the dead of winter and I’m like, “I’m sick of this jacket.”
FLEMING: Yeah, truly. And also doing the door of a nightclub, I’m out in the elements. So tips: a good thermal, whether it be silk or Uniqlo, that HEATTECH stuff.
KIRKPATRICK: HEATTECH has saved me many a time.
FLEMING: Oh my god. Without a silk thermal and a HEATTECH, I would still be an ice cube. Also, those fleece-lined stockings that look like you have on a sheer black stocking?
FLEMING: Those are incredible. I want to write them and see if they’ll do a full bodysuit in that.
KIRKPATRICK: That’s a good idea. A catsuit would be gorgeous.
FLEMING: But thermals, base layers, a cashmere sweater and tights are good.
KIRKPATRICK: Those are good tips. I didn’t even think about you having to stand at the door outside in the worst weather possible. That is a whole different type of challenge that most people’s outfits don’t have to face.
FLEMING: Yeah, totally. I did get two good ski suits and they help.
KIRKPATRICK: I like going full ski bunny core at the door. I need to see it in person. I’m going to wait for the coldest night of the year and then come see you.
FLEMING: Please do. Come by and give me a little sunshine.
KIRKPATRICK: I would love to. You’ve been working in the fashion industry for so long, how have you seen the it change over that time, for better or worse?
FLEMING: Well, the democratization of fashion is a two-edged sword. It allows for representation of body types, ethnicity, and color. When I started, there was Mugler, [Vivienne] Westwood and [Jean Paul] Gaultier, brands that would go in and break away and give fuel to this moment. On the bad side, it’s this predatory view on it—that it’s a means to an end and not a form of art and expression that can fuel people’s creativity and their joie de vivre, which is fueled by our devices and the way the world is going now. It’s like a dilettante coming in and you don’t know the difference between a trench and a car coat, but you have these opinions that are nonsensical. Meanness has also been elevated to this place where you can be as vicious as you want. Then, once you’re being canceled, you can do an apology video and come back all renewed until you do it again. It’s weird, but it’s the way the world is going now politically.
KIRKPATRICK: Definitely weird. And these designers that you’re modeling for at the beginning of your career, culturally, we don’t allow for artists like that anymore. You talk about a [Thierry] Mugler or a Vivienne Westwood or a Gaultier, and these are once-in-a-generation talents that were given carte blanche to be experimental and go against the status quo of the times. So much of fashion has become corporatized in this way where they don’t want risk. I think that the audiences have followed suit in that way.
FLEMING: If you are there for a selfie, you are at the service of them. It isn’t your creativity that’s being put into it and a harmonious marriage of a creative spirit. It’s every man or woman for themselves. And it’s like, where do we go from here? AI? I can’t sink my teeth into AI because it’s basically a glorified cartoon.
KIRKPATRICK: Even cartoons have a real hand and mind behind them. They still feel more human than whatever we’re getting from computers. I feel like they’re trying to erase humanity from art completely, which isn’t art anymore.
FLEMING: No, it isn’t. There can’t be an app for everything.
KIRKPATRICK: Yeah, sometimes you do just have to talk to people. Can’t replace it.
FLEMING: From being at nightclubs, I’ve seen the shift of the lack of skill of interpersonal communication.
FLEMING: Sometimes you go into the club and there are people in front of the DJ booth with their phones up and they’re filming. And it’s like, “But you’re not going to dance?”
KIRKPATRICK: Are the kids dancing these days? I’ve heard no.
FLEMING: [Laughs] It depends on the DJ, it depends on the space itself, because sometimes it’s just a photo op. “I have to prove that I was there,” and there’s proof that you were there, and there’s the joy that you get from being there in that moment that’s forgotten. I guess they don’t have the perspective of being cheated by that dynamic.
KIRKPATRICK: Maybe it’s because I’m a millennial, so I grew up half my life completely without computers. I didn’t have a cell phone until I was 16. I always feel like the things that I do that I heavily document, I end up feeling not as emotionally connected to as the things that I was fully there for.
FLEMING: Yes. It just seems like you’re encased in this world of marketing yourself.
KIRKPATRICK: Right. Self-branding almost.
FLEMING: Yes, because 10-year-olds know about branding, and it’s just like, “Wait a minute, are you not just going to go out and play?” “No, I have to film it so that I can monetize it.” What is this monetization about, getting a tote and a free t-shirt?
KIRKPATRICK: Fingers crossed. When I hear these reports about Gen Z not dancing or not hitting on each other, part of me can’t blame them because if someone was documenting my every move, and it might turn into fodder for TikTok, I would also be very wary of what I’m doing in public. It’s a panopticon. You’re removing all of the freedom of living.
FLEMING: And the spontaneity of the moment. Lindsay Lohan and Paris Hilton were at the tipping point. They could still be a little messy and learn from life because you learn from your mistakes, and if your failures are filmed, they live forever, and it’s a stop gap in your progression of a psyche and a personality. Sometimes you see kids and they’re in the Pooh Shiesty and a hood, and it’s like, if it was us in this moment being filmed constantly, I don’t think that I would have the strength to not want to have my autonomy and not be monitored.
KIRKPATRICK: Definitely. I’m thankful so much of my life cannot be Googled or traced back to me.
FLEMING: Truly, back when I started in the late ’80s, early ’90s, there were people who were documenting, but they were friends and you saw them coming because it was a camcorder.
KIRKPATRICK: Nothing good can come from that.
FLEMING: Are we giving predators a new in?
KIRKPATRICK: Baffling. I’m curious how you feel about Gen Z rediscovering you and your body of work through social media. I’m seeing Connie edits on TikTok all the time now.
FLEMING: Yeah. I’ve been posting stuff from our podcast, The Cutting Up: A Kiki with Connie and Lina . Like, comment, and subscribe.
FLEMING: There has been this engagement through TikTok, but it started to happen before with Tumblr.
FLEMING: I would get DMs and it’s like, “Oh, I admire you and your body of work.” It does give you a chance to look back fondly. When I was coming up in the field of performance, art, music, and fashion, it was about getting your foot in the door and leaving the door open for those to come behind. And it was really beautiful because I did accomplish that. There was a door and there was a space for my ilk to come through behind me. It was weird, and I still grapple with it, but wow. I can pat myself on the back for throwing caution to the wind and just doing it.
KIRKPATRICK: Yes, and taking the risk to be so public like that. You’re trailblazing for all these girls and guys who are making their big runway debut. Obviously fashion still has an incredibly long way to go in all departments, but just the way that we’ve seen these trans supermodels come into the mainstream, I’ve been amazed.
FLEMING: It’s been such a great thing to witness. Being able to be honest—because when I started it was like having this secret over you, it damaged so many. I made a choice not to do that because I saw how it broke down so many talented and beautiful people. I was just super happy about being able to take hold of my trans-ness. I was happy that I wasn’t evil, or mad, or a detriment. I knew what I was and I went out and I was doing something about it. And to see now that these new kids can be full within who they are and the beauty of that and being able to reach out to so many people, it’s incredible. When I started, it was like, “Women aren’t going to be able to connect with you and you’re going to destroy this.” And to see now that that was bullshit.
FLEMING: It’s an expansion of whom you can reach, and who sees your label as inclusive to expression of who you are and that you too can join in. It allows so many to be inspired.
KIRKPATRICK: Definitely. I think what Gen Z is resonating with in these early photographs is seeing someone like yourself being so joyful and transparent. You presented such a fierce version of femininity that I hadn’t seen before on the catwalk. It expanded my mind about womanhood and all that it can encompass.
FLEMING: Yeah, because it was also Mugler and Westwood.
KIRKPATRICK: I’m thinking of you and Mugler specifically.
FLEMING: Because he saw you as the best version of yourself and dressed you so that you could express yourself because his clothes weren’t about constricting. They were constricting, yes. I have lost consciousness three or four times. [Laughs]
KIRKPATRICK: For glamour though, for the beauty.
FLEMING: Yes, that was fashion. But within that encasement, there was a way for you to shine because they not so much glorified, but enhanced in a way that you saw what was beautiful about you. That’s such a wonderful gift that those designers of that time gave out to the world. And when you love yourself, you can then go out into the world.
KIRKPATRICK: Throughout your career, you’ve been called an It-girl, what does that title mean to you?
FLEMING: It meant that I worked my way up. I’d found the yellow brick road, I’d found Oz, and being called an It-girl was sort of the moment when you click your heels and you realize that you could always go home. Because they were like, “Oh, as a Black trans person, as a this or as that,” and to go in and express myself and for them to lift me up and say, “This is a representation of us,” it was like, “Okay, I did something.”
FLEMING: I did something and I can hold my head up and say, “Yes, I am part of this community and I’m not just an observer or a poser. I am here and I am contributing to this community that I admire and love.”
KIRKPATRICK: You embody all of the artistry, creativity, and fashion of that time. That is what is so It-girl about you.
KIRKPATRICK: Please, thank you . You’re the one who did it.
KIRKPATRICK: You did the damn thing. Well, thank you so much. I’m a huge fan, so this means a lot. And I’m going to come see you at Le Bain this winter.
KIRKPATRICK: I’m going to come see the fits.
Source: Fashion
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