The Clothes That Make the Man

Photo by Possessed Photography on Unsplash

Once upon a time, Eddie Izzard (who was at the time presenting as a man) said, “They’re not women’s clothes. They’re my clothes. I bought them.”

This is how easy the logic should be: People can wear whatever they want to wear. Clothing has no inherent gender. Our modern definitions of “what men wear” and “what women wear” are social constructs that are in constant flux.

But emotions are not logical, and our perceptions are based on an accumulation of experiences. Those experiences include messages from society about what is acceptable and what isn’t.

One of the major ways our larger culture communicates those messages is through mass media entertainment. Today I’m going to talk about how comedy has shaped my perception of clothing, and of what I’m “permitted” to wear.


Before I get into it, I want to make something very clear. I say this because, in the past, I’ve been accused of being humorless. I’m going to mention a bunch of examples, and for most of those examples, I see the humor in them. This article isn’t about pounding my fist on the table in leftist outrage; it’s about describing the overall pattern of how humor is used to reinforce cultural standards.

It would be disingenuously facile to argue that each example was actively created to support an insidious toxic masculine conspiracy to further marginalize anyone who is coded male but who wants to step outside the box. Most do not.

Most are bred from that context, but their creators lack the reflective depth to be an active part of such a conspiracy. They’re deemed funny because of the culture. They’re straws on a pile of hay, and each individually is fairly harmless.


I was born in 1968. My first memory of routinely seeing a man in a dress is Klinger in the TV show “M*A*S*H” (1972–1983). The premise is that Klinger was hoping to get sent home from the war on a Section 8 (Mental Health) dismissal. He wore a dress to prove that he was insane.

Every week of my childhood, for years, I saw this message. My parents loved M*A*S*H. But while my father forbade us from singing the lyrics to the movie theme, “Suicide is Painless” (the TV version was instrumental), we never had a serious conversation about Klinger’s clothing.

Because, I suspect, my father thought it was just as funny as the rest of the TV audience.

The seed that a man wearing “women’s” clothing would be enough in itself to warrant an insanity defense was planted in my young brain. It was watered routinely throughout the years.


The reason why Klinger was dressed like that was rarely mentioned on the show. At some point, it just became “the way Klinger dressed”.

Later, Jamie Farr stopped wearing the clothing on the show, in part because Klinger took over Radar’s old role but in part because Farr’s children were being teased. So Farr was aware of the effect of his weekly outfit in his own home.

In the movie “Airplane!” (1980), there’s a brief joke that I feel is attached, at least tenuously, to the Klinger role: Ethel Merman has a cameo as Lieutenant Hurwitz, who has PTSD and thinks he’s Ethel Merman.

I get the humor. It’s funny. It’s also part of a steady cultural drumbeat.


I was 12 years old when “Bosom Buddies” premiered. The premise of the show: Two men need a place to live in New York. The only place they can find that they can afford is a woman-only apartment building, so they dress up like women.

There is no question about their sanity: They are sane. They are opportunists. The subliminal message is that men will dress like women if it means they can get what they want.

I watched “Bosom Buddies” every week.


Around that time, I also discovered Monty Python’s Flying Circus. I had a group of friends (all boys), and while they were “nerds” like me, they still played a part in reinforcing masculine attitudes. We collectively loved Monty Python.

While the “Bosom Buddies” and Klinger cross-dressing jokes were fairly one-dimensional, Monty Python’s message was more complex.

The general defense is that Monty Python was an all-male troupe and, hence, any women had to be played by a man. That’s not 100% true: Carol Cleveland appears in 31 of the original 45 episodes, but her appearances are short and, frankly, fairly misogynistic in their own right. When the troupe wanted eye candy, they went with Cleveland. When they wanted anything more complex, they put on a dress.

Still, given the generally absurdist nature of the show, it’s difficult to declare most of the bits as being clearly problematic. Again, it’s more about the steady drumbeat of messaging, the idea that “a man in a dress” is inherently funny, than about overtly transphobic messages.


There are two bits that do stand out to me as crossing that line into transphobia or homophobia, only one from the show proper. That one is “The Lumberjack Song”, an upbeat and lively tune about a lumberjack who dreams of pressing wild flowers and dressing up in women’s clothing.

What really drives home the idea of masculine enculturation with “The Lumberjack Song” is the behavior of the choral singers. Each of Michael Palin’s verses are echoed by a group of male singers who grow increasingly uncomfortable, and by the end just abandon the song entirely.

It is in the contrast between Palin’s character’s joy and the discomfort of the other men that the darkest part of the message sits: Do this, and you will be ostracized. Even the woman (played by Connie Booth, who appeared in six episodes) bursts into tears.

The funny part: The incongruity of a manly lumberjack wanting to prance around in women’s clothing. Even that part, though, reinforces that there’s something funny about a man in a dress.

The unfunny part: The ostracism, which is what gets the biggest laughter. Including from pre-teen me.


The second bit that comes to mind is from one of my favorite movies, “Monty Python’s Life of Brian”. In it, one of the heretofore male characters admits that she wants the group to call her Loretta and treat her like a woman. She insists on the right to have babies, even though it’s clearly biologically impossible.

The “right to have babies” parody has been echoed recently by anti-trans bigots who want to mischaracterize the experience and beliefs of transgender women. Many transgender women have reported that hormone replacement therapy sets off a monthly mood fluctuation cycle similar to the one that cisgender women have; for the sake of simplicity, they’ll say they now have periods.

Bigots have used that to scoff that transgender women believe they’re bleeding every month. This is a biological impossibility: If you don’t have a uterus, you can’t have menstrual discharge of blood. Perhaps the bigots are also confused because transgender men can have menstrual discharge (and hence the bigots think that transgender people talking about their menses are transgender women).

Regardless, though, the scoffing in “Life of Brian” that transgender women can’t have babies implies that transgender women truly believe they can get pregnant. This is a gross and hurtful parody of the truth.


While “men in dresses” as a comedic trope surely appeared earlier, “Some Like It Hot” (1959) is often mentioned as an early mainstream use of it. These are opportunistic men: Tony Curtis and Jack Lemmon are on the run from the mob, and dress up as women to hide.

In 1975, Tim Curry wore drag in “The Rocky Horror Picture Show”, playing “a sweet transvestite from transsexual Transylvania”. As depictions go, this is one of the more positive ones.

In 1982, Dustin Hoffman wore drag to get a TV role in “Tootsie”.

In 1984, “Bachelor Party” included a bit about a man realizing the “woman” he’d gotten a blowjob from was really a “man”.

In 1984’s “Repo Man”, Miller relates a story where he knows John Wayne was gay because he answered the door wearing a dress.

In 1985, “Real Genius” tucks in a single line: “Professor Hathaway, are you wearing makeup?” followed by one character making a “he’s gay” hand gesture. (He’s wearing makeup because he’d come from the set of his TV show.)

From 1988 to 1995, The Kids in the Hall followed in Monty Python’s footsteps of playing women’s roles in drag. Also, the “Womyn” sketch features the Kids (not in drag) playing poker and wishing they were women.

In 1993, Robin Williams wore drag to get around a custody restriction in “Mrs. Doubtfire”.

“Friends” aired from 1994 to 2004. Kathleen Turner appears three times as Charles Bing/Helena Handbasket, one of Chandler’s parents. Despite being played by a woman, the character is consistently referred to using male-coded language.

The BBC show “The IT Crowd” (2006–2010) includes a blatantly transphobic episode.

And the beat goes on.


Positive messages about male-coded people wearing “women’s clothing” are relatively rare, prior to the last decade or so. Credit goes to “All in the Family” for its treatment of Beverly LaSalle; even Archie Bunker shows some compassion. This was two decades before “To Wong Foo: Thanks for Everything, Julie Newmar” (1995) put drag queens on the big screen as protagonists.

Also, “Community” (2009–2015) deserve a special discussion. Its first season, it maintained the cultural drumbeat of “man in dress = funny”. But as the series continued, Dean Pelton (Jim Rash)’s character evolves from a one-dimensional “we know he’s gay because he wears dresses and goes to seedy bars” joke to being much more complex and accepting of his identity as both gay and gender non-conforming.

I’m not fond that the show didn’t clearly disentangle the topics of sexual orientation and gender, but I definitely laud the show for growing up as it progressed. And it didn’t surprise me to learn that Jim Rash apparently privately accepted his own orientation during the run of the program.


Again, the point is not to pound my fist in outrage. “Life of Brian” remains one of my favorite films; it also gets meta, having a scene of the men actors playing women pretending to be men. Comedy is complex, and it’s far too easy to reject an entire work because of some missteps.

This is about drumbeats and representation: Until I was an adult, the message I got nearly every time I saw a man wearing a dress in comedy was that the humor was the dress. Such men, the message went, are either opportunists or gay.

By the time I got to “To Wong Foo”, one of the reasons I wanted to see it was the incongruity of seeing manly men Wesley Snipes and Patrick Swayze in drag. I had completely internalized the transphobic message that my society had drumbeat into my brain.


These days, there are more positive representations of men and male-coded people wearing dresses. But I personally still struggle with how I see myself. As I write this, I’m wearing a t-shirt and a skirt; if I were going to go outside, I’d change into pants.

This is the effect of internalizing social judgments: I have learned the rules of what is expected of me, and though I know that it is illogical, it shapes my self-perception.

Emotions aren’t logical, and emotions aren’t easily swayed by appeals to logic.


I’ve been told I’m misreading Monty Python, or Mrs. Doubtfire, or other examples from my list above. That the creators didn’t mean to be transphobic.

I don’t think most of the examples on my list are cases of actively, consciously transphobic people thinking, “Hey, let’s create something that reinforces what real men should be doing by laughing at men who aren’t doing it.” That’s absurd. Comedians and comedy writers write jokes they think are funny; they don’t (generally) write jokes with the intent to hurt anyone. And many of the cases above, in isolation, aren’t hurtful in themselves.

Indeed, the fact that comedy writers thought that it would be funny to put two men in dresses as a premise for an entire TV show illustrates how deep the problem was. Such things are the symptom of a cultural disease, not the cause.


I’ve been told I don’t “get” comedy: I would reverse that challenge. Successful comedy is a direct product of the society that makes it successful. Hurtful jokes that rise to the top do so because of hurts that the society, with a more sober face, wants to inflect. “They didn’t mean to hurt anyone!” No, I’m sure they didn’t. But they leveraged social hurt.

I’m thinking now about South Park’s episode “Board Girls”, in which a man pretends to be a transgender woman in order to have a better chance to win an athletic event. The South Park defender would argue: They are clearly making fun of the bigoted idea. Matt and Trey are not, themselves, being transphobic.

But in bringing this up here, I’m not arguing that they are. Whether the comedy is being transphobic or the comedy is satirizing a transphobic attitude, either way it is only successful because the transphobia exists.

That said, though, and speaking generally (not about South Park specifically): Often it is the case that people leverage “Hey, it’s just a joke!” as a way to sneak in their biases.


I’ve heard fellow transgender people speak of the harm done by thrillers like “Dressed to Kill”, “Psycho”, and “Silence of the Lambs”, where villains are shown wearing women’s clothing. And I agree that those can be harmful, even when the characters are meant to be cisgender men.

But I’m concerned that we downplay the harm done by comedies. Because comedy includes the reinforcement of social values by mocking what society deems worthy of mockery, it communicates that: This is what society deems worthy of mockery.

This is, indeed, why more conservative people resist shifts to comedy. They want to continue to mock. They want that permission.

I am now focused on using exposure to men in dresses to overcome my internalized programming, but with half a century of programming, it’s a tough climb. Part of that climb, for me, is acknowledging the harm that some of my heroes have done to me.

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