OCTOBER 25 2017

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 BOOK
NOW
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. ‘Ta­a­a­aste.’”

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 BOOK
NOW
mention in the New Yorker, she says
she never heard about it, and laughs. 

Connie at the Love Ball at Roseland Ballroom, 1988 or 1989.

Born in Jamaica, Fleming moved with

BOOK
her mother to Flatbush, Brooklyn NOW
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 BOOK
stopped going to gym class entirely, NOW
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. 
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NOW
The Boy Bar Beauties in 1986. Photo by Matthew Kasten. 
 

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Gina, Raven, and Connie of the band FDR DRIVE. Photo by Doris Kloster.

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 BOOK
stuck. It wasn’t long before people NOW
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.

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Connie and Keith Haring at an FDR Drive performance at The Pyramid, 1989. Photo by Tom
Eubanks 
 

Codie Ravioli, Gina Vala Vetro, Connie, and Becky backstage at the Palladium, 1990. Photo by
Tina Paul. 
 

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 Connie by Francesco Scavullo, 1990.

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
BOOK
trans person], you’re a drag queen,” NOW
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 BOOK
Fashion Week show. Vivienne NOW
Westwood subsequently cast her in
shows and George Michael cast her in
his video for “Too Funky.”

Test shoot for Azzedine Alaia book, 1988. Photo by Steven Meisel.

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Connie walking for Thierry Mugler, S/S 1992.

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Connie and Jean­Paul Goude for Interview Magazine's Valentine Issue, 1993. Photo by Steven
Meisel.

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 BOOK
NOW
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. 

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NOW
 Connie for Thierry Mugler's book Fashion Fetish Fantasy, 2000.

“I had to develop a
persona, someone BOOK
NOW
 who was no-
nonsense and
demanded
respect.”
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.]” BOOK
NOW
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 BOOK
personification of the wall she built up NOW
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. 

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BOOK
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Connie for Candy Magazine, 2012. Photos by Danielle Levitt.

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.” 
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NOW
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.” 

Connie, Catherine Baba, and Honey Dijon by Mario Testino for Australian Vogue, 2016.  
 

BOOK
NOW
 Connie by Paul Steinitz, 2012. 

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
BOOK
years. (“It’s like the mafia,” she said, NOW
“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
Culture 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
Hotels 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
Food & Drink herself over the years—self-
confidence, fearlessness, and
resilience.

Along the way, Fleming and her

Happenings mother reconciled and are now very
close. She didn’t want to overwhelm
her mother with just how much she
accomplished, explaining, “I would
Specials 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
Shop BOOK
hope. [Laughs.]”  NOW
 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.” 

All Culture HOTELS

WRITER

ELENA FELDMAN

PHOTOS COURTESY OF

CONNIE FLEMING

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