A Personal History Of Dress Up

Cross-dressing, on Halloween and other days

I crouched down in the aisle of Target, looking both ways, and picked up the cheap wig. The Jungle Explorer style was a knock off of Lara Croft in Tomb Raider. The dark brown “hair” didn’t quite match my wife Lauren’s, but the chopped bangs that would drape over my forehead looked similar. I was going to have to unravel the long braid and trim the excess length.

It wasn’t the first time I’d worn a wig. Lauren and I dress as couples for Halloween. When we paired as Fry and Leela from Futurama I simply wore an orange wig spiked with hairspray along with my own red jacket, white T-shirt, blue jeans, and sneakers. Lauren really goes the distance: in addition to a tank top, black jeans, and boots, she cut her own cyclopean eye from paper layered over a length of hose, sprayed purple dye into her ponytail, and constructed a utility wrist strap from rolled up cardboard.

This year, I had options. Lauren set out two pairs of skirts that my grandma had given her, next to a blue long-sleeve shirt. I was afraid I’d rip out of the shirt, despite its ribbed material. I ended up going with a padded floral bra because the sports bra I first tried on stretched too widely over my back, and in the front it revealed my hairy nipples. The underwire dug into my ribcage and the shirt only cinched my chest tighter. With every other breath, as I heaved in deeply to replenish the short supply of air intake, I could feel the bra’s clasps bend.

When we were kids, Mom let me and my brother Joe would dress up at home. We wrapped boas around our necks and wove hairclips into our bowl cuts. I don’t remember smudging on lipstick but Mom didn’t usually wear it, so she probably didn’t have any for us to try. Dad called us Josephina and Christina. He thought it was just as fun as when we acted like pirates in bandanas, clip-on hoop earrings, and eye patches. Dad always played with us whether we strutted down the hallway for our catwalk in a fashion show or shot darts behind empty box-forts in a Nerf battle.

Lauren wore two sports bras underneath my loose navy button-up. She tucked the shirttail into my khaki pants, filling out the seat and inseam with her curves. Her long hair was folded up into my orange ball cap that I began to wear during summer when my handyman hat got too streaked with soil and stained with paint to wear to parties.

But it wasn’t my clothes that made Lauren look like me. It wasn’t the scruff. With a stipple sponge she dotted stubble all over her cheeks, chin, and throat. Lauren even added a dot like my beauty mark on the left side of her upper hairy-appearing lip. I didn’t want to look at her, let alone kiss her, because it was too ridiculous to see my grotesque self, like looking at a fun-house mirror.

In freshman year of high school, my Aunt K, who didn’t have any children, brought me and my cousin Jess to New York for almost one week in summer, because she took all her nieces and nephews to a city when they became teenagers. Every afternoon, she would kick us out of our hotel to explore the streets while she took a nap. Jess and I wandered the nearby blocks and visited surrounding buildings. We rode the chipping gold-plated elevators of Trump Tower and lit a wispy-wicked candle at St. Patrick’s Cathedral. We still had time before having to go back to the hotel so I dared Jess to do something ridiculous because we were two bored teenagers. Jess went up to a corner newsstand and asked for a KitKat. When the guy turned around Jess added, “And a Hustler.” I laughed as hard as the guy who shook his head but still sold Jess the candy. Back in our room, Aunt K snored. Jess and I went into the bathroom to share the KitKat. Since Jess had done something ridiculous I had to also. I picked up Aunt K’s dress, put it on, and danced around the room.

I clomped out of our house in my own boots with wool socks just short enough to reveal my hairy calves below the hem of Grandma’s skirt. The autumn air blew up my legs and over my exposed clavicle in Lauren’s sweater. I wouldn’t want to wear those clothes at any temperature. I wore plastic lenses set in a painted pair of pink frames like Lauren’s glasses instead of my own. Daylight Saving Time hadn’t fallen back and so the sun still shone for any of our neighbors to spot us on our way to the party.

A female Fidel Castro met us at the door of the apartment of George Michael (not the singer, but the son from “Arrested Development”) and the Brawny Man who were hosting the party. Lauren introduced me as, “My wife….” Immediately I got weird looks — despite everyone knowing us — followed by suggestions on how to improve my costume, from men in the kitchen.

Cowboy said I should have shaved and worn make up, like he did as Sarah Palin in 2008. Batman (from the Adam West years) said I looked ridiculous. He poked my sock-filled chest without my permission. Before moving to the living room, I wondered aloud who should be calling whom ridiculous, since he was wearing a mask made out of electrician’s tape and running shorts pinned up to his waist to create bulging briefs over gray pajama bottoms like a diaper.

There’s a man in town who wears a skirt. I know his name but I won’t tell, because I don’t have his permission, so here I’ll call him Don. Don’s square bifocals nestle in his bushy graying beard. Often, he wears a blouse, but it’s difficult to tell because it could be a fancy button-up shirt. Sometimes he wears a scarf that matches his skirt of the day. I’ve heard some people say he dresses up as a way to grieve his supposed wife’s death. Others say Don is a nudist and a skirt is the closest he can get to feeling naked. Perhaps he has a psychological condition. I’ve never heard him described as a transvestite or as transsexual or even homosexual. I used to talk to Don every Saturday morning at the farmer’s market when he wore a placard that advocated Take Good Loving Care of Yourself. I’ve only heard him say that he feels free in a skirt. Don is one of those small-town characters; he stands in front of City Hall, where he informally serves as the doorman. Regardless of the day, he will greet you by saying, “Happy Birthday” and give you a penny.

A bearded prom queen in a powder blue dress walked into the party. His chest was too huge with all-too-round breasts the size of volleyballs. Then, in came a bearded blonde princess. His chipped plastic tiara was as fake as his lumpy toilet-paper stuffed chest. Both of them sat with me in the corner; our backs to the wall, defensively and cattily facing the rest of the party.

“I didn’t know you were back,” I said to bearded princess. “How’s your mom?”

“What happened to your mom?” bearded prom queen interrupted.

Bearded princess explained about his mother’s mental illness compounded by hoarding tendencies, and his time spent helping her clean up her multi-story house where she lived alone. Bearded prom queen’s wife, Cheerleader, jumped in to take a photo on her phone and sent it to his mom. He said she’d be surprised.

I started sharing about my mom’s issues with possessions and how she loves giving knick-knacks as gifts. I spent the rest of the party talking to those two other guys about our mothers; women who birthed and raised and knew us as boys; now men who had dressed up as women but who would always keep them as the first women we know enclosed like a tattoo of a heart on our biceps.

Last Halloween, Lauren put age make up on my face. She brushed on dark lines blocking out my future wrinkles. My forehead creased in shock, eyebrows crunched together in disagreeableness, eyelids scratched outward in sun-squinting, and mouth dug from my nose to the edges of my lips in laughter. Lauren spraypainted my buzz cut and her bun silver. I put on her dead grandfather’s newsboy cap, buttoned a shirt up to my neck, yanked a pair of grey sweatpants above my jutted out belly, and slid into slippers. Lauren wore a loose white blouse under a black sweater-vest with an arched-back cat stalking along a fence top. She wore a wool skirt draped down to some no-non-sense shoes. We stuffed our pockets full of Werther’s candies and hobbled out together like I hope we eventually will fifty years later.

On our way home, Lauren told me she talked to another woman at the Halloween party who went on and on about wishing to be a man for a day. The other woman just wanted to know what it felt like to penetrate. I didn’t like for the idea of a man to be condensed to only a penis, nor do I find it especially funny to wear a skirt or a wig or fake breasts, because none of those alone makes a woman. I can’t explain what makes a woman like I can’t explain why I love Lauren. I can just continue to be ridiculous with her as we dress up.


Chris Wiewiora earned an MFA in Creative Writing and Environment at Iowa State University. After graduating, he worked a variety of odd-jobs including crossing guard, gardener, carpenter’s assistant, bus driver, and dishwasher. His nonfiction has also been published on the Awl, the Billfold, the Good Men Project, the Huffington Post, the Rumpus, and many other magazines beginning with the definite article “the.” Read more at www.chriswiewiora.com