It’s not surprising that a woman would find a man in a dress to be, well, funny and cute—harmless—but not dating material.
I feel beautiful dressed as a woman. I love the gloss of red polish on my toenails, the breeze of a skirt swirling around my gams, and my hair when it gets long and wavy. Sadly, these days, aside from a shaggy mop of hair, I rarely go all out. But for a time in college, I dabbled in cross-dressing.
And that’s how I met my wife.
My history of cross-dressing begins with my hair.
Growing up, haircuts came from a tight-lipped, barrel-chested bald guy named Joe the Barber. On his feet six days a week in a hobbit hole of a shop that reeked of antiseptic and aftershave, Joe wasn’t the cheeriest of coiffeurs. He kept the blinds shut and the conversation limited to the weather, sports, and local tragedies. Joe held curt, grim opinions about all three topics.
Joe specialized in buzz cuts and simple trims. Young customers got lollipops, but those of age could browse a stack of Playboys by the register. Those early experiences in grooming set the tone for my thoughts on masculinity in general. Men held a utilitarian relationship to hair, met the world with a grimace, and enjoyed porn.
At the suburban, Catholic grade school I attended, boys’ hair couldn’t grow below the collar. The prevailing masculine ethos revolved around sports, bravado, and conformity, which our teachers called “being a good Christian.” While nearly all of my peers became altar boys in the sixth grade, I skipped church, preferred books to baseball, and stayed up late on Sundays to watch It’s Garry Shandling’s Show. One of the show’s running gags was Shandling’s obsession with his hair. It cracked me up to see him worry so much about how it looked.
In high school, my image of masculinity grew, and with it, my hair. The cover photo of David Byrne’s 1994 self-titled album, in which he stands serenely in black with locks to his shoulders, inspired me (I was a huge Talking Heads fan) to do the same. A few weeks later I learned that my straight hair actually has quite a wave to it.
After a few bohemian months, even I had to admit that my mane needed shaping, and my mom convinced me to try her salon. A whole new world of hair care opened up for me. The sleek, ergonomic chair—its deep cherry set off by track lighting and a phalanx of mirrors—made Joe the Barber’s gargantuan metal throne seem like an artifact from some primitive society. Rather than spritzing my hair with a spray bottle as if I were a plant about to be pruned, an old Italian woman with thick arms and soft hands massaged rosemary and tea-tree oil into my scalp.
No, Salon Francesco was nothing like Joe’s Barbershop. The few men working at the Salon used phrases like je ne sais quoi and spoke with their hands. They discussed celebrities and screamed about relationship mistakes and one-night stands over blaring bubble-gum pop music. And while I felt more at ease here than at Joe’s, I knew I didn’t fit in, not totally.
So when I went off to Oberlin for college, I decided to let my hair go, as the guys at Salon Francesco would say, au natural. When I complained about it flopping in my eyes, a girl down the hall lent me a barrette. A simple, boring metal clip. I fell in love.
Finally my hair could just be itself! Better still, the barrettes brought out more of my curl. I’ve always fetishized women’s hair, and I took to spending long moments in front of the mirror, poring over my own. Soon I had a collection of plastic bows and lacquered barrettes sitting in a box on my dorm dresser.
During these first few months at Oberlin, my wardrobe changed as well. I took to wearing flared corduroys and a green silk shirt open at the collar. (It’s fairly certain, looking back at the photos, that the shirt was a blouse. It had darts running up the back.) I wore barrettes in my hair, which I dyed auburn.
By the time my dorm’s traditional Halloween all-campus party came around, expectations were high. What would I wear? Too busy with studies to think of an elaborate costume, I decided to throw on my most boring clothes—a turtleneck, a sweater, slacks—and go as Eddie Bauer. Someone I might have seen at my suburban mall, or walking the halls of my Catholic School on dress-down day. Someone safe and traditional. At this point, that kind of style felt like a costume to me.
A sophomore girl down the hall convinced me otherwise. Tall and attractive, she suggested I wear something of hers—and I couldn’t resist. Though her smirk made me think she found the idea funny, I glowed under her attention. I liked the idea of throwing on one of her dresses, of aping this more lovely, adventurous feminine spirit. I picked a short white dress that advantaged my legs and emphasized my narrow waist.
I don’t have a picture of myself in that dress, which is a shame. Because later that night, sitting in a stairwell smoking a clove cigarette, I met my future wife while wearing it.
After Halloween, I sometimes wore skirts to class and dresses to parties, but no matter what, I always sported the barrettes. Despite that, I didn’t consider myself a cross-dresser or even terribly feminine. I grew a goatee, going bohemian. This, after all, was the vibe that had attracted me to Oberlin, a college famous for its counter-cultural history.
The safe space of Oberlin’s campus enabled my dabbling with barrettes and dresses. Sure, a few slim-minded bigots scoffed and called me a freak or transvestite. I stood up to them, as I did to the kids who used to ridicule me for being a bookworm. But for the most part, no one mocked me for being effeminate, though many assumed that I was gay, that the barrettes were part one of my big coming-out. That wasn’t an unusual Oberlin story.
And it was this assumption that led me to stop. It turned out that even my friends thought that I was closeted, that they linked cross-dressing with homosexuality.
Hell, even I had. My favorite professor, a historian, had wavy hair that he wore tousled just so. We often dished about our ’dos—how the weather impacted our wave, and what plans we had for our new look, should we cut our tresses short or grow ’em long. It shocked me to find out that he was dating a Chinese professor, a lovely young woman. I had pegged him for gay.
Just as my wife, upon our first meeting at that Halloween party, figured me a sensitive, feminine gay boy who wanted to be friends. What I saw as dates she viewed as somewhat awkward hangouts. When she found out I like-liked her, she backed off. I wasn’t her type. And it’s not surprising that a woman would find a man in a dress to be, well, funny and cute—harmless—but not dating material.
I began to understand why, that first night I donned a dress, the girl I borrowed it from had such a funny air about the whole thing. She thought my quiet exterior hid a queen. In a way, she was right. But not in the gay way, which she and everyone else seemed to think.
The biggest event on campus was Drag Ball. For several hours one spring night, the Student Union building became a three-floor celebration of all things sex. A sexual-health room supplied unlimited condoms and showed how-to videos on female ejaculation. The hot and packed disco pumped the bass while near-naked bodies writhed in cages. Professional drag queens from nearby Cleveland and far away New York City judged the runway competition on a main stage. The party was a wall-to-wall crush of sweaty, tipsy undergrads in a gender-bending masquerade.
Freshman year, I shaved as much body hair off as I could—face, legs, chest, arms, armpits—along with many men in my dorm. When we were done, the bathroom looked like a surrealist art installation, the sinks covered in hair. I showed off my smooth skin with a short skirt and frilly blue halter top. Sophomore year I went as a geisha, my junior year as Cat Woman. But even then I dialed it back from my freshman extreme. I never shaved my hair again, or showed so much skin.
After my freshman year, the barrettes went away. I continued to dress up lavishly, but only at special times, and even then with a twist. For the following Halloween I was the Bride of Dracula. When my mom came to visit I asked her to wear a suit, then escorted her to a dinner party in a gown. I performed a striptease at a talent show: I began in a woman’s teddy and ended in a pair of tighty-whities stuffed to ridiculous proportions—embracing both masculine poles, I guess.
During this time I realized that my crush on my now-wife was not going anywhere. I became what she considered me from the start: a friend. We exchanged letters over the summers, and corresponded by email during a difficult semester she spent abroad. When she returned to Oberlin my junior year, my romantic expectations of our relationship had been shelved along with the barrettes. I saw her as another of my female friends, of which I had many, perhaps because I wasn’t the type to take advantage of a woman’s friendship.
Not even when, during a pre-dinner low, she suggested we take a nap in her thin dorm room bed. I never made a move, not wanting to screw up the pleasant intimacy that had developed between us. It wasn’t until several naps later, when we touched accidentally and she didn’t back away, that I knew she felt more than just friendly toward me.
Then the tables turned. She began to long for me, while I acted aloof. I became the guy who didn’t want to be tied down. For my final Drag Ball I went as the Master of Ceremonies from Cabaret, who had come to represent a more comfortable masculine archetype to me: dapper, androgynous, and perhaps bisexual—hell, I had kissed a guy or two in my time at Oberlin—but still definitely interested in, and pursued by, women. The guy has “Two Ladies,” for Christ’s sake. He’s living the dream, unencumbered by relationships—a true free spirit, I imagined.
After years of on-again, off-again romance, she and I married and had a child. In the past decade I’ve donned a dress on a handful of occasions, for a party or just the hell of it, to dance with my wife for old time’s sake. I still love the feel of it, but now approach cross-dressing as a form of role-playing. Fun for a while, but not something I would do every day. My sense of gender play has settled down, and so have I.
I used to worry that I’ve gotten too conventional with age. Perhaps I have. But I’ve also realized that, after growing up with such a rigid definition of masculinity that never quite suited me, I reacted by swinging in the opposite direction, and now have come to rest in a position of my own.
Although I was too nervous and unsure of myself as a boy to excel at sports, I’m now far more comfortable as an athlete. I’m a speedy runner and an accomplished Wiffle Ball player. I’m equally comfortable filling a few traditionally feminine roles—staying at home to care for my son, cooking the majority of the dinners, acting as navigator rather than driver on car trips.
My wife cuts my hair now. When I don’t want to be bothered with it, I ask her to buzz it short. Often I let it go long. I love feeling relaxed about it. No matter how I wear it, it looks great. (Right?)
Looks like my inner Garry Shandling lives on.