I am driving in a car with a man who is wearing a skirt. This is a first for me, and while it may make for an arresting opening sentence, it is not, in reality, so very unusual. One of the few things that anyone knows for certain about trans-gendered people is this: there are quite a lot of them. The term has an elastic meaning: it includes everyone from men who get a kick out of occasionally wearing panties under their business suits to transsexuals who, by means of hormone treatment and surgery, are going through the long and difficult process of aligning their bodies with what they believe to be their true gender identity. In a city as large as Toronto, we probably rub shoulders regularly with both, and with many of the points in between.

The man in the skirt, who just thumped his left slingback down on the clutch as he shifted from third to fourth, is a cross-dresser. He has no personal interest in hormone treatment or surgery. He doesn’t want to realign his sexual identity. He’s comfortable with it—which is to say he is quite happy being a heterosexual male who likes to occasionally dress as a woman. He seems relaxed about this. As is his wife, so he tells me.

Lecture “en femme” was terrifying until he screwed up his courage, put on a dress and went to work

He’s not at all concerned with the connection most men make, or think they make, between masculinity and potency. He’s interested in the connection between gender and power, but the notion that he is somehow less powerful—as a teacher, a husband, a friend, even as a lover—because he wears a camisole from time to time is laughably irrelevant to him. He’s not going to get hung up on sexual stereotypes that are hopelessly out of date—if ever they were in date. Nor is he all that hung up on body hair—so I note as I contemplate the wide, hairy back of his hand at rest on the gearshift. We’re doing about 130. I am thinking, This is interesting. Men tend to leave their hand on the gearshift, whereas women shift gears and then move their right hand back to the steering wheel. Until this moment, I didn’t know I knew this.

My driver describes him­self as a “committed” cross-dresser, but, as is the case with trans-genderism in general, cross-dressing defies easy calibration, and part of its confusion has to do with the confusing way society responds to it. If it’s Marlene Dietrich in a dinner jacket, it’s risqué and dangerous and sexy. If it’s a gorgeously exotic drag queen in a bias-cut satin gown, he might become the spokesperson for a mainstream cosmetics company. But if it’s a regular guy—a man in a blue paisley blouse and tan skirt who weaves fairly aggressively through lanes of traffic, and who, when we pull off the DVP and stop at the light at Castle Frank, quietly exclaims, “Well, hello there,” as a particularly beautiful young woman crosses Bloor Street in front of us—it can be a little unsettling. For some reason.

Michael Gilbert is a professor of philosophy at York University, a writer, a speaker and an activist in gender education. He sometimes complains, in a good-natured way, about being too busy, but he would likely have no idea what to do with a more restful pace of life. He’s a member of PEN Canada and was active in the Writers’ Union of Canada. Through his consulting company, Paradox Communications, he gives workshops and speeches to companies and institutions on how to turn internal dispute into organizational creativity. He is the chair of SexGen York, a committee that handles policy issues relating to York’s LGBT (lesbian, gay, bisexual, trans-gender) community and a member of the university’s President’s Advisory Council on Human Rights. He is the book review editor of Trans­gender Tapestry, a quarterly devoted to “all things trans,” and was a member of the board of the Gender Edu­cation Alliance.