For his 32nd birthday, Jake DuPree bought himself some lingerie.
“I just really wanted a red piece,” he says. “I had a maroon piece but it wasn’t the power that I needed. I needed a red, passionate moment so I was really searching for something that spoke to me.” And he found it: the limited-edition Regalia Skylar set from the London-based Playful Promises. When it came in, DuPree tried the high-waisted, lacy set on and it fit perfectly. Since he didn’t have any new boylesque gigs coming up given the global pandemic, he decided to do a little photo shoot, setting up a self-timer and ring light.
The photos went up on May 1 to much acclaim from his followers, but when the brand unexpectedly posted the photos to its own Instagram account saying that the genderfluid performer was “causing heart palpitations,” opinions from its over 300,000 followers were divided.
One follower said that they would never buy the garment as they didn’t want to be “seen in a set made for men.” The brand responded, as it had done many times in the comment section of the post: “Were you previously unaware that all garments can be worn by all genders?”
While the label shut down criticisms with blunt retorts, DuPree ignored the vast majority of it, reveling only in the good. This small instance of recognition was important for him; it was a moment of him being acknowledged and praised for letting himself truly shine. A moment that brought back thoughts of his childhood, playing in his late grandmother’s nighties.
DuPree was raised in Newport, Arkansas, with a farmer for a father and a schoolteacher for a mother.
“Newport was a town of about 7,000 people,” the dancer says. “There’s three, maybe four stoplights now.”
While the stories of many queer children in small towns can be tragic, DuPree didn’t have that experience. Though he describes himself as an effeminate child, his parents were both extremely supportive—his mother had been a dancer growing up. And in his maternal grandmother he found true refuge.
“She was sort of like my safe space in a way,” the performer says, describing his grandmother as the most “traditional, Southern woman” that you can think of. As she figured out DuPree’s tastes, she would buy him Barbie dolls and allow him to play in her costume jewelry. “I feel like who I am now is the same little kid that I was back then. Over the years, as you grow up, you have to hide those aspects of yourself.”
After high school, possibly in part due to playing in his grandmother’s things as well as an eye for aesthetics honed by Old Hollywood (DuPree was a fan of Fred Astaire, Gene Kelly, Marilyn Monroe, Josephine Baker, Hedy Lamarr, and more) he headed to the Savannah College of Art and Design on a fashion scholarship. A chance meeting with that year’s Miss Dance Florida, who was also attending school at SCAD, changed his path, pushing him to meet the college’s dance instructor and switch his major to performing arts with a dance focus.
“It was really the missing puzzle piece that completed me,” DuPree says. And while there was certainly something new about studying dance, it also incorporated his years of childhood training as a gymnast. But before long, he was exploring something else.
After two years in New York City performing in contemporary dance companies, DuPree relocated to Los Angeles. There he dabbled in musical theater, notably getting cast in CATS, where he fell in love with makeup and the ability to transform into a character. This would come in handy when, in 2017, Cosmopolitan came calling with an almost ludicrous request: Do you want to be a unicorn?
“It was this delusional character who thinks they are uber famous and everyone is beneath them,” DuPree laughs of the gig, which was for a project called Glitter Fantasy. “I was allowed to come in and create this costume and improv. I was just being crazy and silly and over-the-top mess on camera.” The series was virally successful and, more importantly, allowed DuPree to explore his own femininity again. But as his star rose, elsewhere things suffered.
In part because of the new feminine persona DuPree began to explore, his romantic relationship at the time dissolved. Six months later, the Glitter Fantasy gig ended, and what felt like an upward trajectory abruptly halted. So, in need of a respite, DuPree turned back to makeup.
Anyone who knows anything about burlesque knows Dita Von Teese. She is, for all intents and purposes, an icon of the form. And she personally trained DuPree in doing her infamous champagne glass number.
The gig was a part of Von Teese’s Von Follies show at the Roosevelt Hotel in Hollywood back in September 2018, and even DuPree’s route to that was circuitous: After returning to makeup, DuPree entered a 10-week local drag pageant in West Hollywood to feel artistically fulfilled. For his performance numbers he began to integrate burlesque, sometimes recreating shows he’d seen at the local Tease If You Please show, and other times making up his own. He won the $5,000 pageant, as well as the respect of key burlesque performers who pushed him to audition for Von Teese’s show.
“When I got the callback for it and they told me I was doing her champagne glass number, I was thinking I was going to be one of the people helping pick up her garments,” DuPree says. “And she was like, ‘No, you’re going to do it.’ I just sobbed in front of her and said ‘This just doesn’t happen.’ And she just looks at me and says ‘No, it doesn’t, but I’m very happy that you’re going to be doing this.’”
Since performing in that show and bringing down the house, DuPree has performed in Tease If You Please’s Valentine’s Day show, in addition to doing sets in London, Mexico, and Canada. He is a part of a growing number of boylesque dancers nationwide that are getting booked all over. And so, in part because of that career, and in part because of the journey to it, he needed that red, lacy passionate set from Playful Promises.
What he didn’t need, or care to acknowledge, were those who had opinions on whether he should or should not be wearing it.
“Overall, some of those comments were so ignorant,” DuPree says. “It’s just people afraid of change and of just accepting others for who they are. I wish that they would realize that me just being happy after going through all of these years of struggling to express myself and finally having the platform to do that and getting positive attention—that is so nice. Like, why waste your time writing negative comments when we’re literally in the middle of a global pandemic? There’s a lot more important things to be mad about than some guy on Instagram wearing lingerie.”
To read more, grab your own copy of Out's Pride issue featuring Atlanta-based musician Damez as the cover on Kindle, Nook, Apple News+ and Zinio today, and on newsstands June 30. Preview more of the issue here. Get a year's subscription here. The issue was guest edited by photographer Alex D. Rogers.