The night Adore Delano won the Glitter Ball, I found the perfect crew-neck sweat shirt. At once transfixed and distracted by two-year-old episodes of RuPaul’s Drag Race, I was multitasking. I clicked away from commercials for hair extensions and fake eyelashes on logotv.com to pore over men’s gym style guides and dreamed of the fall, when premium athletic wear would go on sale. The drag queens had stirred up something in me, but it wasn’t the urge to dress like a woman. It was a love of active menswear I’d never been able to express.

In my three-months binge of Drag Race, while Violet Chachki experimented with new ways to cinch her waist, I experimented with backward baseball hats and letterman jackets. Under the influence of sequins and glitter, I figured out which boyish colors went best with my skin tone: navy, brown, gray, and dark green. Raglan became my favorite word. I read about expansion gussets that enhanced the feel of cotton sweat shirts without loosening the fit. At the age of twenty-seven, I learned how to tie boat shoes. I bled breaking in my inaugural pair, like a new queen strutting in stilettos for the first time.

I absorbed the transformational, aspirational language of RuPaul’s lexicon and translated it into my own terms. “Anybody who can step out of the house with a pair of heels and some lipstick on their lips is my hero,” RuPaul has said. My hero is the person who can step out of the house in soft pants and sneakers with no interest in athletic activity of any kind and only the desire to look good.

A gay man alternately tortured and comforted by reserve and self-hate, I’d long convinced myself that I looked unnatural in traditional menswear: whenever I wore collared shirts and straight-leg pants, I assumed people thought I was trying too hard. It took the great insight of drag—that self-presentation we assume is natural is an act—to make me believe I could dress like a man.

On his podcast, RuPaul talks with onetime icons and resilient B-list celebrities about all the times they remade themselves. His favorite topic of conversation is the age of twenty-nine, the year when Saturn returns to the same place it was when you were born, signaling vigorous upheaval. On Drag Race, RuPaul speaks in mantras and affirmations with both winking irony and total earnestness. I was seduced by this one: “When you become the image of your own imagination, it’s the most powerful thing you could ever do.”

Drag is a second chance at boyhood. It’s playtime and dress-up redone with the self-possession of uncloseted adulthood and the knowledge that playtime and dress-up are the only things that matter—that everything is artifice, that all outfits are costumes, and that anyone who isn’t laughing isn’t worth your time.

It’s this serious commitment to unseriousness that powers RuPaul’s world. A reality competition series in the tradition of America’s Next Top Model and Project Runway, Drag Race takes all the genre’s conceptions of self-promotion, hard work, and merit-based fame and makes an absurd, heart-wrenching joke out of them. Every season, fourteen drag queens battle each other for host and head judge Ru’s approval in design, modeling, dance, acting, comedy, and marketing challenges. The situations are consistently ludicrous—like choreographed musical preflight safety videos for Glamazonian Airways or productions of MacBitch and Romy and Juliet or any of the elaborate infomercials for RuPaul’s books, records, and podcast.

Yet when Ru makes the bottom two queens lip-synch for their lives at the end of each episode, the stakes couldn’t be higher. Desperately mouthing the lyrics to an Ariana Grande deep cut in order to earn another week on the only televisual stage that legitimates your commitment to self-expression is an act of survival more urgent than making fire on Survivor, more momentous than an American Idol coronation ceremony.

In the drag spirit of revisited boyhood, Ru asks the final four queens every season to look at pictures of themselves as little boys and to give their bullied, closeted, pre-queen selves advice, words of wisdom from the other side. It’s the ultimate exercise in self-love. “Stay strong. Don’t let other people tell you how to act,” they say. “It’s okay to be different,” they wish they’d known twenty years sooner.

In my closet, I have no violent childhood bullies or homophobic family members no longer in my life or friends or lovers lost to AIDS. My baggage is nylon: soccer shorts so loose they were always on the verge of falling off, running pants with the tragic silhouette of JNCO jeans, and a track jacket I wished I could wear year-round.

The advice I have for my boyhood ghost is something that’s never come out of a drag queen’s mouth. To him, I say, it’s okay to fit in—it’s okay to enjoy and flaunt the style of the thing that’s also oppressing you.

• • •

I carried a light blue plastic toy wrench around with me everywhere I went from the ages of three to seven. I chewed on it. When I wasn’t holding it, I laid it down next to me, not unlike the way a little girl might lay down her doll to put it to sleep or change its fake diaper. The toy wrench was my teddy bear, my special blanket. It came from a toy tool set I otherwise had no use for. I didn’t see the fun in make-believe home repair. My obsession with the wrench was a purely aesthetic one: I thought it was cute. The hammer, the screwdriver, the pliers—they didn’t do it for me. The wrench had style. It had elegance.

Six months after I finished catching up on all of Drag Race herstory, I recovered the wrench from the remains of my childhood bedroom. I was cleaning out my things before my parents moved. I found the faded, chewed-up wrench in the back of a desk drawer and immediately put it into a Ziploc bag to save what was left of its weird magic. The bag went into the only box of stuff I kept.

The box couldn’t fit the other big-ticket item I held onto, a needlepoint canvas my mom made right after I was born. It has my name in big letters surrounded by meticulously stitched images of things my mom thought I’d go on to like in my youth: Batman, a Mets hat, a race car, a basketball. From a young age, I loved to look at the canvas even though I hated all the things on it. I admired its construction and composition, the baby-nursery sky blue and yellow against the man-cave dark brown, the classic, reassuring, Americana sensibility. I had a vision of boyishness as a style and was determined to make it come to life.

Yearning for authentic masculinity, I confused style with substance. Between the ages of six and ten, I thought that if I liked the way Batman and a basketball looked next to each other, then I must also like the things themselves. Deeper than the ambient social imperatives to play a sport or worship a superhero was my own aesthetic taste.

I asked for a Batman I could hold only to find out we had no chemistry. I sat through Knicks games with my big brother in the living room, torturously waiting until I could put on the VHS of Grease again.

I agreed to join a soccer team because I wanted to wear the uniform. The promise of shiny nylon Umbro shorts outweighed the dread of kicking around a soccer ball. When I got my uniform—the smallest one available—and saw that it didn’t fit me, I wanted to quit, but my mom had already paid the league fees. For one season, I cowered on fields across the South Shore of Long Island in an outfit that swallowed me whole. Even worse was the official photo they made me take. In my loose jersey, against a fake soccer field backdrop, I stood with my hands on my hips, sneering. I got my mom to take the picture off the refrigerator, though I knew that she and my dad carried around mini versions in their wallets. It killed me to think of all the photographic evidence of my ill-fitting soccer getup out there and all the people who might see it.

In the wake of my semi-compulsory one-season soccer career, I held tight to a pocket-size blond boy named Max. He was part of the one boyish object I actually liked in practice: the Mighty Max Temple of Venom. The toy was a plastic snake that opened, like a makeup compact, to a miniature adventurescape. The tiny monsters and weapons and dungeons—and Max himself—were all smaller than dollhouse furniture, so fragile and precious, you couldn’t actually do anything with them. You could only marvel at them.

• • •

In my family, the one thing more taboo than a man in heels was a boy in sweats. My mom told me I could never wear sweat pants outside of the house. It was this rule that drove me to drag for the first and only time in my life.

I did it for the thrill of wearing soft pants in public. I was a four-year-old boy with a simple wish: to have sweats on all the time. I hated the little jeans my mom made me wear to preschool. I hated their formality, their structure, their coarseness.

My girlfriends lived the dream. They got to wear fun, comfy leggings and sweat pants to school. I didn’t associate with any of the boys—I talked only to the girls. The teachers told my mom I was a little womanizer in training. They had no idea I was just a gay boy taken in by girls’ leisurewear.

I peed my way into Jessica’s sweat pants. I knew my mom hadn’t yet provided the emergency change of clothes the school asked every parent to give in case their child had an accident, and that she had designated my best girlfriend as my sharing buddy since Jessica was the one kid as small as I was. So I wet myself on purpose and got to be an underdressed princess for half a day. In one special afternoon, I finger-painted, danced, and napped in Jessica’s pink emergency sweat pants with a cozy fleece lining.

• • •

These days, I wouldn’t be caught dead in a girlfriend’s emergency sweat pants. Over two decades free of my mom’s rule and under the tutelage of RuPaul, I’ve become a sweats snob.

The spring of my Drag Race deep dive, I upped my sports knit game. With the careful eye of fashionista queentestants Raja and Detox, I consulted GQ.com advice slideshows. I studied photographs of iconic men relaxing across time, approaching middle age in outfits of youth, from John F. Kennedy standing on a boat in a sweat shirt to Tom Brady lounging on a couch in a perfectly tailored sweat suit. I read about the athleisure movement, the rise of high-end soft pants, and the acceptability of workout clothes in everyday settings. I thought: what a time to dress like an overgrown boy.

Hopelessly gun-shy and terribly cheap, I didn’t actually buy anything until I found the designer of my dreams, the night I watched Adore win the Glitter Ball. He appeared to me in an Esquire.com countdown of fifteen fashionable fall sweat shirts: Todd Snyder, the former senior vice president of menswear at J.Crew who’d gone on to launch his own line of formal and casual menswear. Alongside his suits and dress shirts, Todd offers chic sweats. The signature item of his collection is the pocket crew-neck sweat shirt, a piece he collaborated with Champion to create. Todd’s sweat shirts are durable and delicate, somehow loose and snug. The colors are all slightly washed: vintage white, rust orange, salt and pepper, red snow heather. The bold red, white, and blue C on the sleeve of every Champion sweat shirt is now a slender, gray, mid-century-modern C.

Todd had me at garment-dyed. Before I’d even touched one of his sweat shirts, I’d fallen under their spell. The catch was the price. Todd’s masterpieces are expensive—$98—for a boy on a grad student budget. Still, I treated myself. I chose black for optimal versatility.

I thought my first would be my only, but once I started I couldn’t stop. That gateway sweat shirt was almost as flawless as Todd promised it would be—enough to get me hooked. If Spike TV started a home-shopping network and needed a host for their Todd Snyder hour, I’d be their guy, standing beneath pennants and a shelf of whiskey screaming, “This is a sweat shirt you can wear on the couch or on the town.”

Every month for half a year, I bought one: oatmeal, crimson, mast blue, washed olive, and a special two-tone gray and white.

I figured I wasn’t putting away money for buying a house or raising children like everyone else, so I could buy some beautiful overpriced sweat shirts. Like a newly engaged woman certain her diamond will appreciate in value, I considered my Todd Snyders investments in my boyish future.

• • •

In his book Workin’ It!: RuPaul’s Guide to Life, Liberty, and the Pursuit of Style, RuPaul preaches ten commandments. Incidentally, the very first one: “Never wear workout shoes or gym apparel outside the gym.” My mom would approve.

Earlier in his bible, Ru gives a list of eleven must-have basics for men out of drag, including a fitted blue suit, a skinny black tie, a fitted khaki trench coat, and a blue pea coat. The only items on the list that I actually own are plain white T-shirts and a striped French sailor shirt.

I have my own list—not for queens in or out of drag, but for the grown man looking to do boy drag every day: soccer shorts, a faded blue baseball hat, khaki jeans, white sneakers, and as many Todd Snyder sweat shirts as you can afford.

• • •

After Jessica, before Todd, there were Ralph, Tommy, and Calvin. I momentarily tried to forget my fascination with sweats. From elementary school into my late twenties, I accepted denim as my default bottoms. The few times a year I had to look nice in public, I wore pieces from the standard department store men’s designers: sweaters, khakis, polo shirts. I had the right clothes, but I never looked right wearing them. No matter how small the size or slim the style, the fit was always off—baggy, awkward, made for someone with a different build. Even as I got older and skinny pants and snug shirts for men became the norm, I couldn’t find anything for me. Every brand offered slim versions of everything, yet it was all too long. The slim revolution left me behind. Boys’ button-down shirts were the closest I got to a good fit.

Drag queens struggle twice. Once they’ve arrived at a place of self-acceptance, they face the second mission of finding a trademark style. Every season of RuPaul’s Drag Race features at least one queen who’s just starting her career, who’s still learning the basics and defining her aesthetic. The novice is usually unpolished. She hasn’t learned to control her eccentricity. Her dresses are tacky and her makeup is overapplied. The eighth season introduced a kind of drag novice we hadn’t seen before—a newbie who was too polished. Derrick Barry came on to the show as an already-established entertainer, a Britney Spears impersonator in a nightly Vegas revue. As a Britney look-alike, Derrick was at the top of his game. In full costume, his resemblance to the pop princess was uncanny. On Drag Race, however, his looks always came short. He’d mastered the art of imitation, but he’d never done drag before. Aiming for verisimilitude, he wore ordinary dresses and bikinis and blended his makeup evenly, as if he were an actual woman. He looked like a copy of someone else rather than a creation of his own making.

The queen striving for genuine femininity has missed the point of drag. Drag isn’t meant to look real. The best queens take the same effeminacy they were forced to suppress as kids and present it in its ugliest, most exaggerated form, turning humiliation into glamour. Their wigs are sky-high, their eyebrows painted on, their contouring clownish, their bosoms all over the place, but on the Drag Race runway their ensembles are objects of beauty. They blur the line between supermodel and hot mess, dignity and debasement.

For twenty-seven years, I’d made the mistake of trying to pass as a real version of the thing I wanted to be instead of embracing men’s clothes as the costumes they are. In chasing my fantasy of proper manhood, I was all dignity and no mess. I needed to unbutton my shirts and hang loose. I needed to do what my mom had always told me I couldn’t: dress down.

Watching five hours of Drag Race a day for twelve weeks, I got my mind out of the department store and into the gym locker room. I conjured up images of men in well-worn athletic wear and made them my new icons. I replaced my sweaters with sweat shirts, khakis with sweat pants, polos with T-shirts. I put a baseball hat over my clean, conditioned hair and turned it backward. I became the most authentic unreal version of myself I could be.

• • •

Two years before my love affair with RuPaul, I committed a hate crime against drag queens. My straight friends and I had gone to a bar without knowing that Fridays were drag night. They were all delighted by the surprise, excited to watch the queens. I was secretly weirded out, borderline mortified. I was the one gay man in our group, yet I was the only one who wanted to leave.

I was an unlikely drag hater, for I’ve always loved outsized femininity. I’ve seen every episode of every Real Housewives franchise, I speak in Golden Girls and Mean Girls quotes, and think Showgirls is the greatest cinematic achievement since Grey Gardens, but I had no interest in drag. When it came to train-wreck women, I preferred the real thing. I preferred finding the gayness in straight culture to entertainment that was overtly gay. I would’ve chosen Desperate Housewives and Sex and the City over Queer as Folk or RuPaul’s Drag Race any day. In my mind, drag was another gay cultural form too explicit about its gayness. Out but forever repressed, reveling in my shameful demureness, I wanted my queer fun coded. I didn’t want men dressed as women dancing in my face.

I was ambushed by drag at a bar that wasn’t even gay. Everyone I was with wanted to watch and I knew I couldn’t just ghost them, so I took a seat and watched against my will.

One by one, the queens came out to universal applause. I wasn’t having it. I turned away. When the rest of the small crowd got quiet, I sighed. I laughed. I sighed again. Sighing and laughing were my ways of expressing squeamishness and discomfort, like a little straight boy in middle school calling girls gross.

I didn’t stop sighing and laughing even as the people I was with nudged me and told me to stop. I thought since I was gay and the queens were gay, I could do whatever I wanted. I didn’t yell out any insults. I wasn’t the kind of bully I’d later hear dozens of contestants on RuPaul’s Drag Race tearfully describe as they recounted their adolescences. My offense was, in its way, more insidious, an attack from the inside. My drunken dismissions were so loud that the bouncer kicked me out.

Drag queens want you to laugh with—even at—them, but my laughter was from the very place of seriousness that drag culture wants to dismantle. My refusal to engage with the joke was a form of disrespect.

I didn’t do my time for that crime until a couple of years later when a friend turned me on to Drag Race. She couldn’t believe that the historian of OG Real Housewife Vicki Gunvalson’s meltdowns and Little Edie’s rants had never seen an episode of Drag Race.

The show had the hypnotic low-budget drama of strip-mall lunch sit-downs on The Real Housewives of New Jersey, claims of personal renewal as hysterical and preposterous as Ramona Singer’s on The Real Housewives of New York City, and bigger breasts, sadder grudges, and more harrowing inner lives than any “real housewife” in any city. I watched Alyssa Edwards and Coco Montrese rehash their three-year feud as rivals in the 2010 Miss Gay America pageant. I watched Tyra Sanchez reveal she had a three-year-old son back home. I watched the season four queens remake real-life dads into pregnant, runway-ready moms. I watched Latrice Royale transform herself into a living parade float and imagined what it would be like to see her live. In three weeks, I devoured seventy-six episodes. Through the riveting, familiar filter of reality TV, drag became fun.

Two years after I crashed the party, I wanted an invitation back in.

• • •

The first time I wore my new mast-blue Todd Snyder pocket crew-neck sweat shirt out in public, Darienne Lake licked my finger. I’d been saving the sweat shirt for a special occasion and this was one: the first time I was seeing a contestant from RuPaul’s Drag Race perform live, my first real drag show if you didn’t count the one I’d been asked to leave.

The sweat shirt was the safety blanket covering me in a space where I still felt ill at ease. I was at the gay bar only to see Darienne, and no one else. I hadn’t gone back to boyhood so I could be a better, louder, fiercer, queerer man today. I’d gone back to square one so I could stay there forever. From there, in a sweat shirt I could wear whenever and wherever I wanted, other people’s femininity looked fabulous.

I stood inches from the stage as Darienne came out in a sequined bodysuit. A plus-size queen who gave unmemorable performances and disappointing runway looks on TV, Darienne dazzled in person. I held out a dollar bill, as the drag expert friend I’d gone with advised me to do, and Darienne went right for it. She took the dollar and then came back for more, sucking my finger. It felt less like a tease or a thank-you than a taunt—wet revenge against the boy who’d once laughed at her sisters.

• • •

Tall, sporty men with no names call me handsome even though they can’t see my face. This is what happens almost every time I open Grindr: I’m inundated by spam accounts with stock photos of straight men fishing, lifting weights, and drinking beer.

Whoever created these accounts is preying on the Grindr dream of a masculine man. The Bro Bots are fake, but the profiles they’re appealing to are real—the tons of users requesting “no femmes” and “masc only.”

I’m not an out femme-phobe or masc-hag. My profile has no picture or text. I tell myself I’m on here only to pass time, to chat and never meet up. I’ve thought about putting up a selfie, me in one of my post-Ru looks—backward hat and sweat shirt. I’d have to take the picture in front of the needlepoint canvas with Batman, a basketball, and a Mets hat, holding the chewed-up toy wrench. If taken in the right light, it might even be worthy of my mom’s refrigerator.

• • •

I see jerseys in my future. I’ve recently started to admire the wild pop aesthetic of vintage basketball jerseys. I rediscovered their beauty when cleaning out a box of photographs in my childhood room. I found a picture of me and my brother, at nine and twelve, wearing jerseys at a backyard barbecue. I’m in a 1993 purple-and-orange Charles Barkley, my brother a 1996 teal All-Star Michael Jordan. The men played for the Phoenix Suns and the Chicago Bulls, but their jerseys’ colors are the kooky pastels of Miami art deco. Twenty years later, I have to have one again. It seems like the logical end of my casual menswear mania, the only place left to go: the neon top of a sports legend I know nothing about, whose game I have no plan to ever watch or play, whose big hands I’d rather feel on myself.

Logan Scherer is writing a novel about gay men, reality TV, and West Hollywood.