On the performance of cross-dressing

And the importance of the sex binary

Growing up as a tomboy in the 60s I had a freedom to dress how I pleased that would not have been available ten years before. And what pleased me was shorts and t-shirts in the summer, and jeans and jumpers in the winter. Never skirts or dresses.

Decades later, women wearing trousers is still taboo in some places, and still evolving even in western liberal democracies. It was technically illegal for women to wear trousers in France until 2013, and lots of UK schools still enforce a skirts only policy for girls despite women in trousers being completely accepted by almost everyone.

Similarly, nobody would look twice at a man in a flowery shirt now. But only because hippies challenged dress codes in the 1960s evolving into 1970s Glam Rock and the New Romantics of the 1980s.

And yet, we can still recognise cross-dressing when we see it.

Cross-dressing is never done casually – it’s always a deliberate choice. Sometimes it’s a performance for the individual but more usually for onlookers, and often quite literally a performance on stage or for broadcast.

Cross-dressing for laughs

The pantomime dame comes from a long history of cross-dressing for laughs. The deliberately bad make-up, the comedy bosoms, and the terrible clothes of the ugly sisters – they’re the butt of the jokes, and if the audience doesn’t laugh, then they’ve failed.

We see exactly this dynamic in the Carry On films – Bernard Bresslaw in drag fooled precisely nobody. That was the whole point. Otherwise it wouldn’t have been funny.

Women in men’s clothes isn’t funny in the same way.

When women play the lead in a pantomime – Peter Pan, Dick Whittington, Jack with his beanstalk – they are playing the part of the heroic boy. The underdog who succeeds against all odds. We are meant to believe in our hero, so the part can’t be played by a man because everyone immediately sees that a man is not a boy. And then he’s not the underdog, and the story no longer works.

It is possible for a woman to play the part of a boy for laughs, though.

Jeannette Krankie made a career of it in the 70s and 80s by tapping into that pantomime spirit of not being entirely convincing, and liberal use of the kind of “dad jokes” loved by children. 

Cross-dressing to make a point

Comedy can be boundary challenging too, and nobody used comedy to greater effect than the Monty Python team. Hell’s Grannies was a master class in taking the familiar – the comedy pantomime dame – and asking “what if?”

Cross-dressing for sex

Other performances are more serious. To evoke laughter would be to destroy them because the intended effect is sexual.

When men cross-dress in this way, they present as hyper-sexualised women. Big hair, fabulous outfits – sequins, gold lamé, incredible heels – and make-up to match.

The aim is to be more than a woman. More colour, more jewels, more extreme, more sexy than any woman can be.

Their challenge to women is clear: I am more of a woman than you, beware.

And to men: would you?

To conflate these performances with pantomime dames is an insult. To evoke the same result – laughter – would be disastrous.

Women can cross-dress for sex, too. Consider the Hollywood scene; it’s the morning, and she gets out of bed and slips into his shirt to make the coffee. It’s oversized and hangs loosely, falling to mid-thigh. The male/female difference and her vulnerability to him is accentuated perfectly. Her wearing of his clothes is symbolic of their new intimacy, their sexual relationship.

Popping on a flannelette nightdress simply wouldn’t evoke the same sensual vibe.

When women wear men’s clothes in this way, their femaleness is not reduced, it is emphasised.

In contrast to this, in the 1980’s Annie Lennox channelled her inner Marlene Dietrich to achieve a degree of androgyny.

Both wore recognisably male clothes, but nobody would be fooled that either was male. In fact, both still give off strong “sexy woman” vibes.

Sex is binary and asymmetric

The clothes we wear are an important visual indicator of who we are as we move through the world. The tomboy’s reluctance to wear dresses is more than perversity. She is making a statement of identity. 

The clothes we choose for a performance – when we ask others to “look at me” – will evoke a response from our audience. But we can’t control how we are seen by others, and as a sexually dimorphic species we are rarely fooled about the sex of the adults we meet no matter what they wear.

And when performers cross-dress we are acutely aware of their sex. They can choose to play for laughs or for sex or to challenge cultural boundaries.

But it will always matter if the performer is a man or a woman, and we will always respond accordingly.