Why Women Can Dress Like Men But Not Vice Versa

A woman slips on her boyfriend’s cotton shirt, its shoulders dropping inches below hers, and rolls up the long, long sleeves. She looks even more feminine.

A man borrows his girlfriend’s soft blue pashmina, swinging one end over his broad shoulder. He looks far less masculine.

I am using traditional categories here, and old gender stereotypes, for a reason. I want to know why women can wear men’s stuff but men cannot wear women’s. The two sets of traits were defined in opposition to each other, which should provide a nice clean yin-yang symmetry. Instead, they tilt catawampus.

Is masculinity actually the more fragile of the two, because it is more in need of proving? I can already hear a chorus of yeses from one direction, but I am not sure it is so simple. True, the old notion was that a woman could bear children, ’nuf sed, while a man could never be sure a child was his. Women have that nice symmetrical XX pairing, and the male Y is … complicated. Then you have the cultural standards, by which women simply had to be passive to be feminine, while men had to slay dragons or at the very least, gallop into town on horseback ….

The practical side of me groans at all this speculation. Surely it is simply that men tend to be larger in frame, so there is no workable way for them to wear women’s clothes as freely as women wear men’s? Maybe. But a narrow-shouldered man in a large pashmina will not walk into a South Side bar and get friendly slaps on his cashmere-draped back.

Dr. Mary Ruppert-Stroescu, associate professor at Washington University’s Sam Fox School of Design and Visual Arts, began her career in Paris in the ’80s, back when nonbinary clothing was called “unisex.” “You know how men and women button on opposite sides?” she asks me. “If we made a jacket that buttoned the woman’s way, men would not buy it. If we made it buttoned the man’s way, women would.”

Of course we would. We wear Dad sneakers, granddad shirts, and boyfriend jeans. Can you imagine a guy wearing Mom sneakers, a grandma shirt, or girlfriend jeans?

Maybe there is still enough of a power imbalance that everybody wants to be a guy? (Though I would never.) A woman dressed as a man has a little cachet when she walks down the red carpet. When a man dresses as a woman, it is generally for charity, fun, a drag show, or his private pleasure. Even a man purse has to be extra manly to be legit. (One is made by a brand called Nut Sac; its style name is Dammit. Did I mention trying too hard?)

“Male characteristics are so rich with success and strength,” says Ruppert-Stroescu, “and feminine things are associated with weakness and fragility.” That was underscored in a grad student’s recent research, she adds. He set out to discover just how feminine men’s clothes could get before gay men rejected them. Not very.

Iggy Pop once said, “I’m not ashamed to dress ‘like a woman’ because I don’t think it’s shameful to be a woman.” I smile at the quote—then do a doubletake. Shameful? Is that what this is about? The longer I think about this, the more the imbalance disturbs me. I wear my husband’s shirts and my grandfather’s robe, and when my stepfather died, I kept his Seven for All Mankind jeans. I take real pleasure in wearing this stuff. Also in using power tools, swearing, and drinking bourbon. But when my not-exactly-hard-drinking husband tried to order a banana daiquiri in a pub, I did a facepalm.

How culpable are heterosexual, cisgender women in keeping men boxed in?

I dance away from the question. Soon none of this will matter anyway—gender categories have blurred, and computers will be able to custom design for a particular body. I suspect I will miss the ability to transgress. Why? Because it is (and this makes me ashamed) a rush. One Halloween, I was visiting a friend, and we went to a party on the spur of the moment. Having no costume, I borrowed clothes from her husband, pinned them in place, tucked my hair under a cap, magic-markered a beard. Amateur night. Yet when I walked into a room of strangers in a city where no one knew me, I felt like a guy (or at least what I think I would feel like if I were a guy). I moved more freely, spoke louder, felt far more confident. I manspread.

It is tough to imagine a straight American male feeling thrilled to be taken for a female.

Until recently, and with the exception of deliberately outrageous celebrities, there has been only the slightest symmetry in pop culture. Watch older movies, and you will see young women scripted to be adorable by pulling their ponytail through a ball cap and guys scripted to cook with a frilly apron tied on crooked. And … that is it. Stops right there.

“The vast majority of hyped-up “unisex” clothing lines have conspicuously left out even completely basic skirts and dresses, despite their being logistically simpler/cheaper to produce than the heathered sweats and hoodies, graphic tees, and occasional lumpy denim,” notes Nora Whelan in a Playboy article, “Why So Many Men Chase Skirts, But Won’t Wear Them.” She is puzzled, because “nearly a century after Marlene Dietrich and Katherine Hepburn first led films in slacks and suiting, the general cis- and heteronormative male population refuses to wear skirts.”

When I persuaded my husband to wear nightshirts instead of pajamas, he said more than once (his version of effusive) how comfortable the nightshirt was. He has not worn pajamas since. Skirts and easy dresses are also far more comfortable than all that pants and belts rigamarole. If Scottish kilts became cool here (a cultural appropriation that would enrage the Scots), could that finally be an entrée? Because if we are going to go nonbinary anyway, guys might as well feel breezy. It has been an awfully long time since togas.

Taking one final stab at understanding, I ask Dr. David Lisak, a psychologist who works with men and thinks a great deal about norms of masculinity, for his take. Why such resistance? Several men in Whelan’s article admitted that they would like the comfort of wearing something … tubular … but felt they would be risking their reputation if not their life.

Lisak thinks a minute, then swerves toward prehistory, when our hominid ancestors were forced into the savannah and had to hunt for food. “We didn’t have big fangs or long claws,” he points out, “but we were good scavengers. Working as a group, we could throw stones and sticks to drive a lion away from its kill, then move in and grab some meat. Animals are completely petrified when you throw stones—they can’t see the stone coming, and they can’t throw one. So all of a sudden, you have this animal that can move power across time and space. That becomes how hominids survive.” The catch? “To pull it off, they could show no fear. If one of the males started fidgeting or dithering, they would fail. The only way it was going to work was like a football huddle, everybody grunting together—studies show that testosterone rises in those huddles—and absolutely nobody demonstrating any weakness.”

I am listening hard, envisioning caves and blazing fires and the poor lions driven from their dinner, but it takes me a minute to see the connection. Then it clicks: A man can never behave like a woman. He must be brave and strong and silent, a reliable member of his group, ready to put the common goal ahead of any private qualms. Any show of emotion, fear, softness, nervous chatter—in other words, normal human behavior that reads as weakness—means everyone will go hungry.

Retailers are going to have to hang a steak from every manskirt.


Read more by Jeannette Cooperman here.