Kyle Farmery is not who you think he is. "I prefer 'he,'" Farmery says. "I'm a dude. I'm someone with a boy's personality who happens to like makeup and pretty things. But I still think like a dude." Virtually everything about Farmery, a staple in the New York nightlife scene and a blossoming figure in the fashion world, defies traditional expectations--including his age. In person, Farmery--with his striking facial bones, classic sense of style, and highly precocious poise--presents as a kind of latter-day Marlene Dietrich, that timeless icon of androgyny and Old Hollywood glamour, and the inspiration behind the exclusive shoot that accompanies this story. As Farmery gracefully moves through a space, his natural black hair pulled back tight to accentuate his face, and his arms draped in fur to go with his laced-up heeled boots, he schmoozes with almost everyone, in the eloquent voice of a veteran New Yorker. It's a shock to the system when he tells you he's 21 years old.
"I never acted my age, and almost all of my friends have called me an old soul" says Farmery, who was born in Manhattan and raised in TriBeCa. His father is a sculptor and his mother is a realtor, social worker, and activist. Both were always supportive of not just Farmery's sexual orientation (he identifies as gay), but his lifelong rejection of typical male clothing. "Boy's clothes were so boring," he says, adding that he was roughly 3 when he wore his first "dramatic dress," at his sister's birthday party. It was Farmery's parents who eventually helped him enroll in the Frank Sinatra School of the Arts in Astoria, Queens, a performing arts high school founded by Tony Bennett and his wife, and a place where Farmery could begin his detailed, obsessive journey in learning about aesthetics. His education in color and proportion have stuck with him to this day. "I look better in pants than a skirt because a skirt cuts me off mid-knee, whereas if I show my whole leg I look taller," he says. "And then color-wise, I have green eyes, and I learned quickly that if I wear orange eyeshadow, for example, they'll pop my eyes most."
As for Farmery's public precocity and established place on the nightlife scene, it's a full-blooded New York story. Already enamored of international trans icon Amanda Lepore, Farmery attended one of Lepore's calendar signings at 13, making an impression that, thanks in part to his mother's open-minded support, led to a lasting and influential friendship. "He was so knowledgeable for someone so young," Lepore says of Farmery, whose interest in fashion was so intense that, after school, he'd often leave the train at the 59th Street station and walk all the way home down 5th Avenue or Broadway, passing his favorite stores and absorbing trends he saw in windows. Soon, as Farmery's mother gained trust in her, Lepore took Farmery under her wing as a kindred-spirit-cum-protege, taking him to parties and events and exposing him to a world of vibrant, like-minded personalities. "It was fascinating to see how he could get into clubs without a problem," says Lepore. "People that age just don't do their makeup that well or carry themselves like that. By 15, he fit right in with people who were more experienced, and he was so grown up. It was incredible to watch."
Another nightlife mentor Farmery found early on was Kayvon Zand, a local legend who's been a promoter and club regular for nearly a decade. Entirely unaware that Farmery was only 15 when they met, Zand also saw the potential and uniqueness of a fiery teenager unafraid to, say, wear heels on the subway, at school, and at the club. "For the times, it was monumental to see someone that young so comfortable in his skin, and so brave in his social life," says Zand (who, like Lepore, was a trusted guide in the eyes of Farmery's mom because he doesn't partake in drugs). "And he was so observant. Kyle isn't necessarily impressive to me by the way he is now--he's impressive to me by the way he's always been."
But there are still pressures that come with being a nightlife fixture at any age, especially if you look like Farmery. Because he can present as female, many people immediately assumed he was transgender, or presumed to tell him that being trans was his destiny. "People still think I'm going to transition," Farmery says. "They've told me, 'You'll get through it one day. It'll catch up to you and you'll figure it out.' " But as many know, and as Farmery soon found out firsthand, being trans is not something someone simply decides one day. Propelled in part by people's expectations, Farmery did try taking estrogen and testosterone blockers at 16, a process he discussed with Lepore. "We talked about it a lot," Lepore says. "I advised him that if he was going to do it, he should do it when he's young, while he's still developing, like I did. He was undecided at first, but he realized he didn't want to do it." Adds Farmery, "I grew almost an A cup within nine months, and I didn't like the way my body was transforming. I've always prided myself in being androgynous. But I don't regret it because it helped me to relate to people who are going through transitions or starting hormones, and I've actually helped a lot of my friends who are going through it because I've had part of the experience. I was just reassured that it wasn't something for me."
Through all of this, Farmery was still attending high school, and also dating his first boyfriend, who helped him fully embrace the singular self that Lepore, Zand, and so many others ardently admired. "He was the complete other side of the gender spectrum of being a male," Farmery says of her boyfriend. "He was a 220-pound bodybuilder and I was this seemingly feminine gay guy. We were of totally different worlds. I always believed that I would only be loved as a girl because, you know, who's gonna love a gay guy in makeup and heels? But it took someone like him telling me that I'm not only going to be looked at as a girl--I'm a guy and my personality is the best thing about me. Him saying that, something that nobody else could have said, sort of convinced me that what I'm doing isn't wrong." When it came time for Farmery's prom, that same boyfriend, who lived in Toronto and found Farmery via Instagram, drove eight hours to New York to be his date. When he and Farmery entered together that evening, the entire room stood up and applauded. "It was crazy," Farmery says. "Beyond crazy."
Since then, Farmery's life has been an upward journey of stylish successes, thanks to his ambitions and his enduring knack for networking. After high school, he left New York to attend the London College of Fashion, and while he didn't much care for the curriculum (the unstructured, "self-directed study" wasn't his forte, he says), he parlayed his nightlife experience into paid gigs, and broadened his social network to an international scale. He quickly befriended artist and nightlife bigwig Daniel Lismore, and hosted parties and events for drag superstar Jodie Harsh. He was flown to Vienna for Life Ball, where he rubbed shoulders with Grace Jones; he pulled together an impromptu burlesque show for DJ Larry T, which also booked him a gig in Sweden; and he fell head over heels for London's neighbor, Paris, where, naturally, he continued to expand his friend circle. "One of the most important things I learned from Amanda at a very young age was to simply be nice," Farmery says. "Help everyone, and they'll help you back."
And that help continues to pay off. Farmery's 14,000-plus Instagram followers don't just track him because he looks like a million dollars--they follow him because of the work he's put into solidifying a sterling reputation. His mentors and instincts have led him to interning for the likes of Zac Posen and Patti Wilson upon returning to New York, which in turn have landed him modeling and appearance gigs for Marc Jacobs, Mac Cosmetics, Baja East, and more. He chooses to largely keep his methods of income mysterious, but one thing that's certain is Farmery is regularly booked, be it for stylist and makeup jobs, appearances at parties hosted by Ladyfag and Susanne Bartsch, and collaborations with outlets like Lookbook and Italian Vogue. ("I've taken nearly every opportunity that's come my way without ever being a hooker," he quips.) Farmery says it's very difficult for him to settle into doing one thing, which perfectly suits his hard-to-define persona.
"I think he's on his way to becoming an international fashion icon," says Lepore. "In one way or another, he's just going to get bigger and bigger, and I think he'll focus on one thing after a while."
Zand, however, seems intent on seeing Farmery maintain his nondescript identity, both personally and professionally. "Kyle's story is his own, and it's a very unique story of what we can be as a society," Zand says. "It's important that all of these options are left open, and I think Kyle represents that--you may not be this shade of red, you may be this other shade of red. At the end of the day, when you put yourself out there publicly like Kyle does, and you get involved, you can inspire people and you may even pave people's paths."
If Farmery had to choose one person with whom he identifies most, it would be David Bowie, who "was super feminine in his own way," Farmery says, "but still a guy--still a dude." And still, the dude in Farmery can give him brief moments of pause. "Sometimes I'll lay in bed and be like, 'Oh god, am I really going to do this?'" he says. "I can still get a little nervous before I start putting on makeup. But once I'm ready, I've usually taken so long that it's just time to go. I get into these situations, but they always end up great, and I'm in the zone. And I guess I am fearless. I can get a little hesitant, but, you know, I've never stopped myself from doing anything."