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Image Source: Benjamin Stone

How Does a Drag Queen Get Ready?

Ever Wondered What It's Like To Get Ready For Drag? 1 Queen Sashays Through the Process

"The amount of witchcraft that goes into drag is insane," proclaimed Jan Sport, burgeoning New York City-based queen. We are sitting in her 250-square-foot bedroom in Hamilton Heights, where the cool A/C air ricochets between the assemblage of purple bed sheets and her vanity table a few inches away. Drag makeup and wardrobe can get hot, she explained, but it's a good thing she's not much of a sweater.

"Frankly, I never expected to do this as my job; I was terrible when I first started," she said. "I was kind of lucky that I don’t have a terrible face for drag, so I didn’t look too busted, but it was a journey. I didn’t start out with the name Jan Sport, either. I was going by my boy name, Charlie Mantione as Kris Jenner. I just loved performing. Once people caught on that I had a knack for it, it picked up from there."

Two years later and Sport's Instagram following has reached the dozens of thousands. Her schedule is jam-packed with shows six days a week, if not more, and especially during Pride month, many of which she performs with girl group Stephanie's Child. "When I am in drag those days, I’m in it for eight to 10 hours, if not longer. It really is my life. I eat, breathe, and sleep drag."

But today, perched in front of her vanity — one of the few black items she owns in a sea of lavender — Sport walks us through the amalgamation of steps it takes to get ready for a night out. Is it witchy? Not necessarily. But magic? That's a big yaaaas.

"The amount of witchcraft that goes into drag is insane."

Step 1: Beat Your Face (Then Repeat, and Repeat Again)

"Drag makeup is so different from regular makeup," said Sport. "It takes me about an hour and a half to get ready, and that part takes the longest for sure. If I want to go crazy or I'm really feeling the fantasy, I'll give myself two hours."

But that's now, after hundreds of hours of practice. In the beginning, despite dabbling with makeup from Sephora and MAC here and there, it wasn't so easy mastering the tricks of the trade. Creating the "illusion," as she calls it, of a lovely bone structure or bigger lips or a smaller nose, or all the above, took time. "I've watched a lot of YouTube videos and adapt it to my own face. I also picked up a few tips from my drag mom Alexis Michelle — the family resemblance is strong. She was on [Ru Paul's] Drag Race and has taught me a lot."

Like how your base makeup — foundation, concealer, contour, correctors — should always start as a cream before setting with powder. Or that alternating between your correct foundation shade and one two shades lighter can bring the features you want to highlight forward. How orange color correctors work wonders at canceling out dark shadows from a beard. Oh, and that eye shadow makes the best highlighter.

The first step, though, is shaving her entire face — including her eyebrows. "A lot of drag queens glue down their eyebrows with a medical-grade adhesive, but my skin became allergic to it and I had a rash all around my eyes," said Sport. "The drag makeup covered it up because it’s so full coverage, but it burned, so I made the decision to shave off my eyebrows. This is my job, and it might not look good when I’m a boy all the time, but I can draw them on and look presentable when I need to. It’s not a big deal to me. I have RevitaLash, and they grow back in like three weeks."

It's no wonder, then, why she's dubbed her brow pencil as the one product she goes through the quickest ("well, that and my Ben Nye Translucent Setting Powder") — because she uses it in and out of drag. "When my boyfriend wants to go out he'll say, 'Put on your eyebrows, let's go,'" she laughed.

Step 2: Pile on the Purple Pigment

About 35 minutes in, after Sport primes, corrects, covers, conceals, highlights, contours, blends, and sets, sets, sets, it's time to add in some color. She has one in mind.

"Purple was my favorite color growing up," Sport said. "I had purple shirts, backpacks; I wanted everything to be purple. I didn't care what anyone thought, honestly. I was very open as a kid, and I was lucky to have really supportive parents. I was always like, ‘I’m going to do me.’"

Now, she's the third queen in drag trio Stephanie's Child, who's other members include Rosé and Laguna Blue. "We all have our set color. They are pink and blue, and I got to pick mine. You better believe I chose purple, honey, and it's expanded into full-blown craziness ever since."

Finding the right shade of eye makeup, on the other hand, has taken some trial and error: "Having purple as my signature color, it's hard," she said. "Purple is such a difficult pigment to master and make vibrant. I know there's a lot of drama going on with James Charles right now, but his Morphe Eye Shadow Palette is everything. There's such a nice mix, and the purple is so good. I wasn't sure if Morphe was going to discontinue the product after sh*t hit the fan, so I panicked and bought three. Using this color — and especially when I do the cut crease, my favorite part — it makes me feel extra feminine."

Step 3: Draw on the Drag Details

We're inching toward the one-hour mark (that shadow and detail work takes werk, OH-K?) and Sport is on her final makeup touches. She's already lined her lips one-third of an inch above and below her natural crease, filled them in with the pencil, and topped it off with gloss. "A natural look," she conceded. Though, Sport knows to stash an extra lipstick in her purse. "That's the only thing I have to really reapply throughout the night, mostly because of the microphone and talking into it."

Next up: falsies. "Thank god — I feel naked without them," she said. "Now, I don't use lash glue for my lashes. A good drag queen trick and secret is weave bond. It dries quicker and keeps the lashes on; it's much more durable. Then I put on a little mascara. . . just the tips." With that, she gives a wink — and finishes up the face: "I’m a big fan of setting everything with hairspray — it’s not great for your skin, but it locks everything into place. It won't budge all night."

"I’m a big fan of setting everything with hairspray — it’s not great for your skin, but it locks everything into place."

Before we move on to wardrobe, and because drag is all about the illusions after all, Sport wants to do one last thing with her makeup: "Draw on some tits!"

"It’s really interesting the way queens accomplish the look of cleavage," she said. "First I’ll shave my chest to get rid of any hair. I’ll take the foundation I used for my face and apply it all over my chest so the color matches. Then I'll take the same brush that I used for my nose contour, dip into that, and draw lines up and out."

Her approach to creating realistic-looking breasts — "and everybody has a different technique to this" — is to do the outline of a martini glass. "If an outfit has a chest piece that's a little higher up, I'll draw them more like a Champagne flute than a martini glass because I want them to be seen. Once we have the outlines, we'll use our fingers and windshield wiper out to blend. As people say, we feel our oats, and just smooth it out to create that shape. Then we'll take the white face powder and fill in the insides of the lines to add some more dimension."

Windshield wiper, windshield wiper, boom: "the illusion of beautiful breasts."

Step 4: Dress To the Nines

An hour and a half has come and gone — it's about the length of time it typically takes Sport to get ready in total, but it turns out she's feeling the fantasy today. Drag queen fashion feeds way into that. . . but it requires a little elbow grease.

"Before I can even put on my outfit, I have to put on six sets of tights," she said. "That’s to hide the lines from the lovely hip pads I put on my body to give me the woman’s figure I want. All the queens have pads that we custom cut ourselves. You can make all different sizes, too. You just order a huge slab of memory foam, or you can get it from a mattress or couch cushion — we call that the "Raymour and Flanigan" — and then we use a turkey carver to cut around the edges."

Sport continued, "You place them near your butt so it kind of looks like cheeks, and then we’ll just lift her up. I like my big mama hips; I love looking like a voluptuous Kardashian — sticking true to my origin of Kris Jenner. Then we just start to tuck everything away, behind, under. Taping everything down doesn’t make that much of a difference for me. Everything just gets squished down there with all of the tights anyway, so if anything pops out, I’ll just tuck [my penis] in between my legs."

"It's really fun dreaming up the designs for big events, actually," said Sport. "We’re drag queens, and the world is our oyster, so we better show up with some good costumes."

Though she can whip up an outfit on a whim if need be, she also works with a handful of clothing and wig designers for bigger events like TV or a gala. She'll share her vision; they'll draw some sketches. Then, they spend hours upon hours in fabric stores (and yes, "throw down some money, honey," she laughed).

"When I’m not performing, it’s all about being beautiful so I’ll wear something nicer like a dress. I won’t wear the outfits I get made for bigger events to my bar shows — you don't want to ruin something you spent hundreds of dollars on. For those, I’ll always do something that’s comfortable and easy to dance in but with a flair."

As you might imagine, keeping costume material in pristine shape isn't easy when you're sashaying and sweating and sweating while sashaying. So sometimes, she brings out the big guns: "If I know it’s something I’ll be in for a while, I’ll get some vodka spray or an alcohol, mix it in with some cleaner to soak, and then just leave everything out so it absorbs the dirt and oil," she said. "Another trick is to put your outfit in the freezer – for some reason that just absorbs everything. You just spray it with alcohol and then put it in the freezer."

Step 5: Snatch a Wig From Your Collection

Image Source: POPSUGAR Photography / Benjamin Stone

Like a proud mom looking at her kids, Sport beams at her arsenal of wigs. There isn’t a crevice in this 250-square-foot bedroom that doesn’t have one in close proximity.

“I probably own 50 or 60 wigs,” she said. “I keep 20 of them out on display — the fancier ones — but then the others are all scattered sporadically around my room. I have some in my closet, under my bed, in my suitcase. It’s funny because my room is decently small for a New York City apartment, but we’ve always gotta figure out where to keep the wigs.”

Like her custom costumes, hand-made wigs are a splurge (which she’s OK with, “mostly because I know I’m not going to be twirling around in them or crawling all over a bar in a Marie Antoinette-type wig”) — which can clock in anywhere between $200 to $350 each, depending on the style or how much hair they use. “The cheaper wigs I can just get at the store that I can style myself but aren’t anything extravagant, but are nice to wear to a show, those are probably $40 to $50.”

Sport has a performance later this evening at Hardware, a gay bar in Hell’s Kitchen, so the priority with her hair right now is keeping it secure. “Wigs can be so heavy, I need to tape it down with duct tape,” she said. “I’ll put on a wig cap first and pin clips underneath the tape to create a firm base. It will not move.”

Another big go-to product is Pump It Up — a stronger hairspray often used in the black community to lay down edges. “I’ll use it if I’m styling a wig for a bar show and I need something serious to help lock it in place. It’s the strongest stuff out there — there’s even a disclaimer on it that’s like, Flammable! Do not use near fire or flame.”

For tonight, Sport decides on a signature look: the half-up ponytail — purple, of course.

Step 6: Nail the Finishing Touches

“Look, every queen needs nails — the pointy ones make you look fierce. Nobody's gonna mess with you wearing these.”

Of course, she says that in jest, but the dangers of being a drag queen — and member of the LGBTQ+ community in general — are very real. Sport continued: “I’m very comfortable with who I am with myself and in drag. Every day you run into people who will say things to you in the street or cat call you to try and make you feel inferior, but I am very confident with myself in what I do that it will never phase me. Anything anyone can say to me about how I present myself or express my artistry — if they have a problem with that, it says more about them than me. It took me a while to figure that out, especially early on.”

She hops on the bed with her clear box of metallic KISS nails and reaches for brush-on nail glue, also from the brand. “I like these because I can just pop ‘em on and go – it takes me like a minute," said Sport. "The only time I won’t wear them is when I’m doing a bar show that I know is going to get really rowdy. I’ve had instances where I’ve lost an entire hand [of nails] — literally lost all five on one hand, and then had all five on my left.”

Step 7: Work, B*tch

Two hours, eight minutes, and what feels like 2,481 steps later, Sport emerges from her bedroom a new woman — and damn, is she a woman.

“When I look in the mirror, I feel invincible,” she said. “A very famous queen once said that drag is like a suit of armor. When you’re all made up, you can do anything and empower other people around you to feel like they can do anything. That’s why I do drag. I love entertaining and performing, and when I have something like this on, I’m able to portray that I’m a star, that they’re a star. That we all have so much love to give.”

“When I look in the mirror, I feel invincible. When you’re all made up, you can do anything and you can empower other people around you to feel like they can do anything too."

In the end, though, drag is more than mere physical transformation – it's also about the kind that takes place within.

“A lot of my friends who knew me before I did drag have said Jan is like Charlie, but louder. When I’m on stage, I’m very ‘on.’ Not that I don’t have a personality out of drag, but I do save my energy for when I’m performing. When I was growing up, I was very much so a people pleaser. I wanted to put my friends’ needs before mine and make sure everybody around me was taken care of before me. With Jan, it’s like, Put the oxygen mask on yourself before helping others. Jan has helped me discover that, which really is life-changing.”