It’s hard to overstate the power, political and personal, inherent in drag, which is the act of transforming how you look in a way that blurs or plays with the presentation of gender. What’s even harder to convey is how much FUN it is, but it is, as I recently found out myself while being transformed into a glammed-out drag dilettante by my friend Colin Self, a Brooklyn choreographer/composer/drag queen. Some of you may have seen (and freaked out over) the ’80s documentary Paris Is Burning or the reality show RuPaul’s Drag Race, so you know that drag allows you to pick a persona and embrace it completely, like playing an awesome role in a movie that you’ve directed yourself.

Most drag artists are into the idea of gender-play as entertainment. The person dressing up usually identifies as being one gender in their day-to-day life, but performs as another, and although drag is considered a part of gay culture, a person can be straight and still do drag. Many queens look and behave very differently when they’re not performing. During the day, Colin works as a barista at a New York City cafe. He sometimes incorporates feminized pieces into his wardrobe, but for the most part, he just looks like a fashion-forward blond guy with cute glasses and great sneakers.

Drag, on the whole, is an exaggerated celebration of difference, and I was really curious to find out what it felt like to harness its awesome powers. During my time with Colin, he made me over as a faux queen, which is the term for a biologically female person who appropriates the look of a drag queen. We decided to go this route instead of making me into a drag king because I wanted him to take me through his step-by-step process—and also because I wanted to wear an obscene amount of lipstick.

I met Colin at his apartment in Williamsburg. We settled onto his living room floor, and as we started figuring out our looks for the evening, he told me what led him to start doing this: “As a kid, I worshipped Celine Dion and Shania Twain—they were making their own worlds. So I moved from Oregon, where I grew up, to Olympia, Washington, where I went to college. I wanted to be a lesbian at that time. I was very effeminate, and the men I was attracted to were butch. I liked this possibility of being in a male-male relationship, but as women.”

Colin Self

Shortly after he moved from Olympia to Chicago in 2009, Colin manifested his desire to be both a man and woman by creating a drag persona. “Olympia musicians like Khaela Maricich and Anna Huff were really drawing these exciting artistic connections between performance and music, and they introduced me to the idea that I could just sing a song in a backyard with a wig and a drum machine and convey something powerful,” he says. “In late 2010, I started going out to clubs and bars in drag.” According to Colin, many queens work within a genre called “realness,” which means successfully passing as a woman, but for the most part, he wasn’t interested in portraying someone hyper-feminine. Colin, who refers to himself as a riot grrrl, was also turned off by the way he felt traditional drag clashed with his feminist ideals: “When I first started wearing wigs, I never wore makeup. I didn’t like drag. I didn’t like what it said about women—women shouldn’t have to have all this makeup and hair. But as I got older, I came to realize that drag is all about celebrating female beauty, and I could represent a sexual, feminine woman in mainstream culture and still be a feminist.” Yet despite how cosmeticized Colin looks while performing in drag, he still uses his own name and is proud of the bits of maleness that he allows to show through, like his Adam’s apple.

Colin in drag. (Photo via Samantha West.)

Colin is a multifaceted performer: depending on the night, he could be dancing, lip-syncing, or showcasing his own music. Along the way, he learned all kinds of fun makeup tricks that he shared with me in our makeover. Although I’m one of the most femme individuals you will ever meet—I wear fake eyelashes every day and dress more or less like Betty Boop—Colin was still able to teach me some amazing secrets. Here’s Colin and me serving ’90s-era, best-girlfriend realness right after we were done:

I think we can all agree that the real winner here is his “bitch” dress, which he scored in a thrift store in the Pacific Northwest, aka prime real estate for the castoffs of grown-up Riot Grrrls. As Colin says, “You either put on an outfit, or a doubtfit.” This is definitely the former.

Colin shaved his face as closely as he could, which he hates. “If you ask any drag queen, they’ll say shaving is one of the more horrible parts of doing drag,” he says. “A lot of people get laser surgery.” Then we set out to queenify ourselves. The first step in achieving the look we’re showing here involves a base of white pancake makeup, which should be applied all over your face. (Colin recommends Ben Nye.) This blanked out our features so that we could build our own contours, like cheekbones and jawlines. After applying liquid foundation, we sucked in our cheeks, packed a big, fluffy brush with dark bronzer, and blotted it into the hollows of our fish-faces.

Where I'm pointing is where the bronzer goes.

We then arranged our faces into HUGE, deranged grins and applied blush to the chubbiest part of our cheeks. Finally, we applied a liquid highlighter to our cheekbones, following right above the line of bronzer and into our hairline. Many queens also use contouring to shape and slim their noses, which you can achieve by applying highlighter down the thinnest part of your nose, stopping before you get to the tip.

Next, in keeping with the drag mantra of “MORE IS MORE,” we put on some wild eye shadow. I learned that a good way to do dark eye shadow without getting it all over your face is to use an index card and line up an edge of the card with your bottom lash line. I pressed it against my face while applying my eye makeup and it caught extra shadow that would otherwise have flown onto my impeccably sculpted cheekbones. It also gives the impression of enormous, almost owlish eyes (but, like, a sexy owl). Applying either individual lashes or a strip to the upper lash line balances out all the makeup and gives it more dimension. Finally, we filled in and extended our brows past the point of reason, taking our cues from Groucho Marx (if he was a hot babe). In case you didn’t already hear me: ANGLES ARE EVERYTHING. But it was also liberating to realize that the results don’t have to be perfect. “God knows that there are a lot of drag queens that don’t look good, but that’s OK!,” Colin says. “No shade. Drag is about diversity.”

We finished off our looks with our respective wigs. “It’s not about good or bad taste,” he adds. “If you know yourself and trust yourself, people will believe it, too. When I put on a wig, it transforms me spiritually, mentally, and physically.” I ended up loving my wigged-out appearance so much that I bleached and cut my real hair in a style that imitated this one shortly after our makeover. Drag actually helped me to see something new about myself that I liked a lot.

Colin had the idea for me to top off the experience with a public performance, which we did a couple of weeks later. Although some queens dress in drag just to go out to clubs or parties, many others choose to showcase the primped and painted versions of themselves through public performance. We decided that I would do a routine to one of Mariah Carey’s classic singles, “Heartbreaker,” at Colin’s insane monthly drag party called CLUMP. CLUMP takes place at a bar in South Williamsburg, Brooklyn. “I wanted to throw a party that’s weird and funny and doesn’t take itself seriously,” explains Colin. “It’s named after a clump of poop, or mascara, or people, like a community of artists and musicians.” It gets super, super packed, so I was really nervous. I hadn’t performed publicly since my legendary lip-sync-and-dance routine to Smash Mouth’s “All Star” in my fourth grade talent show. (At least I had some experience.) Unlike that afternoon, though, I was wearing towering high-heeled boots, an enormous blonde wig, and what might best be described as Richard Simmons’s dream bathing suit. Mine was the last performance of the night, and the party was in full swing by the time I took the stage.

It was definitely intimidating, but there wasn’t much room for nervousness as I stepped up to lip-sync for my life. I felt like I was wearing a suit of outré armor. Between the screaming crowd, the extra inches from my heels, and my general glamouflage, I felt gorgeous and untouchable. I’m pretty confident generally, but performing that night gave me a special kind of power. I imagine it’s only a fraction of how beautiful and confident a genuine drag queen might feel, based on what Colin tells me about his experience performing. “I really feel as though I was put on this planet to spread light and beauty, and when I am onstage, I feel like I am channeling some higher feminine force and projecting that energy out into the world,” he says. “I feel indestructible.” And I did feel inspired in an entirely new way. An audience of at least 50 people watched me, singing along and cheering enthusiastically. The drag parties I’ve attended over the years have hosted some of the most welcoming, fun audiences that I’ve come across in New York City nightlife, and this night was no exception. I guess I got a little too into it, because about halfway through the song, I felt my wig slipping off due to excessive gyrations and dramatic finger-pointing. It seemed better to just go with it, so I ended up head-banging the wig off, then whipping it into the audience, which made everyone freak out in the best possible way.

I have to say, I now have a deep respect for XY-chromosomed people who put so much effort into feminizing themselves. It’s an art, and it’s not easy. For Colin, it’s worth the work. He says being a queen wasn’t so much a choice as an epiphany. “I’d been performing in drag for about a year before I thought of myself as a drag queen,” he recalls. “Then, in 2010, I was performing in San Francisco, and I left thinking, ‘I am a loud, gorgeous, freak woman and I love it.’ I guess you could say I was becoming more aware of who I already was as a person. It was a funny realization. It just kind of occurred to me: why wouldn’t I want to be a drag queen?” ♦