The Untold Story of the Fearless Connie Fleming

One of the few mentions you’ll find of her appears in a 2016 New Yorker article profiling the insurgent, cutting-edge New York City fashion designer Shayne Oliver of Hood By Air. Oliver, in the thick of organizing the upstart label’s latest groundbreaking show for New York Fashion Week, stops to look at a text on his phone: “‘Ooooooh!’ he says, ‘Connie just got confirmed for the door.’ He’s referring to Connie Girl, a legendary New York City doorwoman with a fearsome reputation for being impossible to get past and impossible to book. ‘Taste that,’ he said. ‘Ta-a-a-aste.’”

Connie’s website no longer exists, and beyond that brief, intriguing mention, there is only a scant digital trail: A 2012 Huffington Post headline that reads “Michelle Obama Played By Transgender Model Connie Fleming On Candy Magazine Cover”; blurry videos of her club performances on YouTube; a 2010 New York Times article titled “The Bold Crossings of the Gender Line” in which she shares her perspective as “fashion’s transsexual ‘It’ girl” of the early ’90s; and a 2007 Village Voice article titled “NYPD Busts Ass,” which reports that “police at the station referred to Connie Girl as ‘it’ and ‘that’” after raiding a club where she worked the door.
 
After a private message on Twitter and a few weeks of crossed lines, we managed to connect with Connie by phone, and when we bring up the mention in the New Yorker, she says she never heard about it, and laughs. 

Born in Jamaica, Fleming moved with her mother to Flatbush, Brooklyn when she was five years old so her mother could further her education and make a new life away from Fleming’s alcoholic father. Assimilating into America, Fleming’s school life quickly became a living nightmare. “As a trans child, it was horrifying,” she shared. “From the first day of first grade to the last day of high school, they hated me. I couldn't have cared less. By eight, the world shows its face to you—how mean, how petty, how violent it can be.” 
 
Fleming has blocked out many memories from her youth, but what she does remember are the daily, incessant threats of sexual and physical violence at school. When she started openly identifying as trans, her relationship with her mother became fraught, too. “She didn't understand. It was hard for her to deal with. I had fights at school, and then I would have to fight at home.” Like many others, she found her safe haven in art, specifically fashion illustration. 
 
After several sickening encounters in her high school locker room with the football and basketball teams, Fleming stopped going to gym class entirely, saying, “I didn't think I would survive.” At the end of her senior year, she lacked the gym credits to graduate. With the support of an art teacher who believed in her, she got her art portfolio together, earned her GED, and started taking classes at the Fashion Institute of Technology.
 
During this time, she recalls wandering around New York City with PTSD. To support her education, she got a job at a vintage boutique, and it was there that fate brought her to David Glamamore, an emerging drag performer, and Matthew Kasten, who booked the performers at St. Mark’s storied Boy Bar. Kasten immediately saw Fleming’s potential, and told her, “You’re going to do the show. That’s it.” Fleming had never even expressed interest—she had never performed before, and she had very little confidence in herself. “I didn’t know how to speak or relate to people,” she said. “I never learned it in school. People come to New York City from all over to build themselves back up.” Kasten’s blind faith in Fleming pushed her onstage and into a new life. 

In the late ’80s, eighteen-year-old Fleming, Glamamore, and others came to be known as the Boy Bar Beauties—cult figures in the now-legendary, boundary-pushing downtown club scene that included Limelight, Tunnel, and Palladium.

One night, Kasten off-handedly referred to her as “Connie Girl” when calling her up onstage, and the name stuck. It wasn’t long before people were stopping her on the street. “I turned around and was like, ‘Wait a minute. I’m famous below 14th Street!’”
 
As her name rose in the downtown scene, she found herself on the verge of working with her idols, only to find one after another falling to AIDS. She arrived to the set of a Francesco Scavullo photo shoot ready to work with the famed makeup artist Way Bandy, only to learn he had just passed away. She was invited by Keith Haring to perform a song by Yoko Ono, with the singer herself in attendance. Haring would pass from AIDS-related symptoms soon after.

Then, one day, Fleming stepped off the stage. She wanted to give herself a real shot at being a high fashion model. “If you perform on stage [as a trans person], you’re a drag queen,” she says. “You can’t really be taken seriously. The line was drawn, and it was drawn by people outside of us.” Her goal was never to turn her back on the drag community. “There are only a few employment options available to trans people,” she explained. “You’re a whore, or you can be on stage and perform. There’s no room in society for us. I was super lucky and thankful that I had drag because it was a safe environment for me to transition. [The drag community] took a broken child and rebuilt her. They gave me confidence and a voice, and lifted my head up off the ground, but I had to solidify myself within.” International Chrysis, Salvador Dalí’s protégé, was booked at Boy Bar, and she became Fleming’s mentor through this transition. Fleming is forever grateful to her, saying, “She saw my future before I could even see it myself.”

In this new phase, she started working at Patricia Field’s store while modeling here and there for Steven Meisel and other luminaries of the downtown fashion scene. After hearing about Fleming and seeing photos of her by Meisel, the designer Thierry Mugler cast her in his Winter ’89/’90 Paris Fashion Week show. Vivienne Westwood subsequently cast her in shows and George Michael cast her in his video for “Too Funky.”

Then in 1992, RuPaul’s “Supermodel” dropped, and drag became a fixture of the runways. Just as Fleming was aiming her sights elsewhere, forging a path away from drag, she was lumped into it. She walked for five seasons in Paris and New York Fashion Weeks and became a face of the “trend,” but she could feel the tensions rising. “There were people in the business who hated drag and thought it was dishonest. A lot went into it—self-hatred, homophobia, misogyny…it was always the underbelly of it.”

In Paris, a reporter asked Vivienne Westwood, “You have a man in your show?” Westwood refused to feed into it, answering only, “What are you talking about?” Before another show, a backstage dresser who didn’t want to work with Fleming encouraged a reporter to ask her transphobic questions, which Fleming fielded by changing the subject back to her work. But when she got back to New York, she was told by her agent that people didn’t want to work with her because she was deemed “difficult” for not answering such questions. “It was that feeling of ‘Leave and get out,’ because you weren’t wanted anymore,” Fleming shared. 

Remarkably, Fleming just put her head down and kept going, saying, “You do what you do. You hustle. That’s New York.” She began producing fashion shows for high-end designers, and she found herself working her first club door—for the notorious party promoter Erich Conrad’s party, Poop. She and Conrad were (and still are) like family, and he wanted her to be the face of his club. “I called her La Gioconda [The Mona Lisa],” he said. “She’s so gorgeous. You would want to wait in line just for her. I was so fascinated because she can get on stage and do the most shocking performance, but then she’s very shy off stage. That’s why I put her on the door—that’s the show. [Laughs.]”

Despite the humorous name of Poop, it wasn’t all as funny as it sounds. “At the beginning, it wasn’t cool to have trans people at the door,” Fleming said. “It was like the kiss of death. Trans people were considered thieves, drug dealers, hookers. No one thought they had to respect a black, trans woman. I had to develop a persona, someone who was no-nonsense and demanded respect.” 

And thus, the “evil door bitch” persona was born. She became known as “the meanest gal in town,” but in her view, she wasn’t mean—she was unwavering. Erich Conrad shared: “She takes no hostages. One time I had her do a door at a VIP room and I said, ‘Don’t let anybody up here. Absolutely nobody.’ I think it was a party for Donatella [Versace]. I had to go up there and she said, ‘No. You said nobody.’ I go, ‘You’re kidding.’ And she goes, ‘That’s what you told me.’ She’s the sweetest, most delicious, toughest, softest cookie.”

Fleming describes her persona as “deadpan,” and it required someone with her life story to master it; it’s the personification of the wall she built up to defend herself from constant hate and discrimination. It led her to working at the doors of some of the greatest clubs in New York City history, which in turn cemented her venerable reputation in the city’s nightlife lore. “It got to the point where if you didn’t have a trans person at your door, you weren’t a real club,” she says. 

In retrospect, however, Fleming says that the “tough” characterization is weighted: “Some people couldn’t handle a ‘no’ from a black trans woman. You could see it not adding up in their minds.” With her trademark delivery, she would tell belligerent messes who pushed the limit and demanded entry “no.” In her mind, she was no different than any other doorperson—her approach was “tough but fair”: “If you were drunk and popped off at the mouth, I gave you a chance. Third chance…sorry dude.” 

When asked why the New Yorker called her “impossible to book,” Fleming said with a laugh, “I don’t know! A lot of people have my phone number.” 

With the ups and downs of the nightlife industry, and based on her personal bullshit meter, Fleming has dipped in and out of the job over the years. (“It’s like the mafia,” she said, “You can never really leave.”) These days, she has a hand in many different fields—fashion and art production, modeling, fashion illustration, makeup, wardrobe, and performing from time to time. Fleming now also runway coaches some of the biggest models working today, prepping their walks for Prada, Versace, and all the major fashion houses, and coaching girls as young as 12, saying, “I want them to be fully ready for every opportunity that comes their way. I want to help create the next generation of fearless girls.” From her nearly 30 years as a model and performer who faced impossible odds, she imparts what she had to learn herself over the years—self-confidence, fearlessness, and resilience.

Along the way, Fleming and her mother reconciled and are now very close. She didn’t want to overwhelm her mother with just how much she accomplished, explaining, “I would hold back on things and slowly clue her in. Now she’s super proud. When I did the Candy cover, she was taken aback and proud that I had made a name for myself. She’s pretty happy, I hope. [Laughs.]” 

When asked if she thought of herself as influential for trans visibility, she said, “I don’t think of it that way. If I did, I think I would have imploded.”