What’s So Funny About Peace, Love, and Underdressing?

Most of us discover this part of ourselves early in our lives. Like, EARLY in our lives, usually in childhood. I think most of who we are as adults is formed in that time. I mean, they are called our formative years for a reason, right?

When I was a child I didn’t think I was doing anything *wrong* by trying on every dress I could find. I never thought I was *bad* for wanting to wear the beautiful lingerie I saw on department store mannequins. Despite this, I knew, and I am not sure why, I had to keep this side of myself a secret.

It’s possible I felt that it needed to be a secret because I was borrowing my sisters’ clothes without permission and that in itself was wrong, not because I was a BOY that wanted to wear a dress, if you follow.

I was blissfully unaware that there was anything taboo about who I was or what I wore. I mean, of course I didn’t tell my friends that I wanted to wear what the girls in our class were wearing, but I think that had a lot to do with assimilation. It’s not uncommon for kids wanting to fit in and to do and say and be interested in the things that the “cool kids” were into. The popular boys in school weren’t talking about pretty clothes, so I didn’t either.

As my childhood progressed (and I am talking about being around 7 and 8 years old) I started to connect the dots about this side of me in terms of how the world thought of someone like myself. These revelations further reinforced the need, almost a survival method, of keeping this side of myself a closely guarded secret.

When I was in my late teens I learned that “crossdressing is a fetish” was seemingly the prevailing perspective. But until then, I was taught that a boy who wore girl clothes was HILARIOUS.

I mean, I was also taught that it was shameful and in a way a punishment but those are things for another day. Instead, let’s chat about how HILARIOUS crossdressing is and was portrayed.

Why is this funny?

I mean, it’s not. It never was. A lot has changed since I was six years old. I wouldn’t say we are more enlightened these days when it comes to gender not being a binary but we’re slooooowly getting there. It’s like walking to the sun.

If someone saw a boy wearing a dress forty years ago they would have been mocked and punished. A boy wearing a dress today, well, there is a very good chance they will still be mocked and punished but there will be those who understand the complexities and simplicity of gender identity.

It wasn’t uncommon for cartoons and movies to have “comedic” moments showing a man wearing a dress or lingerie. It was and still is a cheap joke and the writers probably weren’t too interested in gender identity awareness. I mean, look at how racist and sexist cartoons used to be. Cartoons with characters in blackface or mocking women drivers were pretty normal for a long time.

I don’t really remember exactly the first time I saw a someone even remotely similar to me when I was growing up but I know for certain we weren’t represented in a way that I was, well, proud to be associated with. If a character was shown in their underwear it was probably meant to be funny. Most kids watching a cartoon would probably think it was.

But if the character was wearing pink panties instead of, oh, I don’t know, polka-dot boxers? Peak comedy right there.

We were told that a boy wearing pink panties was meant to be funny. So, we learned that a boy wearing pink panties WAS funny.

Again, these years are called our formative years for a reason. But not everything we learn or are taught is right.

A boy wearing pink panties is funny for the sole reason we were taught that it’s funny.

Was this done maliciously? I don’t know. It’s impossible to say. Like a lot of things in entertainment, certain elements are duplicated if they are successful. If one type of movie makes a billion dollars it won’t take long for similar films to be made. If a joke about a boy wearing pink panties gets a laugh… you get where I’m going with this.

How did this start? Oh, I have no idea. But my guess is that this is rooted in the thinking that anything feminine is shameful and embarrassing.

The cartoons I watched when I was very young showed women as bossy or unintelligent or lazy or emotional or bimbos or lazy. Women were fodder for comedy. The entertainment industry was (and still is) predominately white, cisgender men and how women were written is and was influenced by that.

I mentioned early cartoons mocking women drivers but this type of humor was the rule, the norm. Wilma Flintstone was a gossipy housewife who yelled at her husband. Jane Jetson spent all of her husband’s money on clothes.

Mocking women was “funny”. It probably didn’t take too long for some writer to think it was hilarious to attribute feminine traits to male characters with the intention of mocking them. A female character cooking was “normal”. A male character cooking was shameful and an easy way to ridicule him.. and he was probably wearing a frilly pink apron.

Thus began the dangerous and harmful perception that feminine = shame and humor.

Well, not really. The “tradition” of male actors and male characters playing women for laughs goes back centuries all around the world. Essentially this humor has been around for a very long time. Is it any wonder that reversing the perception that crossdressing ISN’T funny/kinky is unlikely going to happen? We’ve got centuries against us.

As I said earlier I didn’t think what I was wearing was shameful but it needed to be a secret. But I never thought that it was HILARIOUS. I knew if I was “caught” I would be ostracized from my friend group. The reason for this was not because of the clothes per se, but because at certain points in your life if you wanted to fit in, if you wanted friends, you had to like the same things, you had to think the same way, you had to enjoy the same music and movies as everyone else. And that extended to what you wore.

But I never thought (and perhaps I was naïve) that there was anything comedic about wearing what I wore and what I daydreamed about wearing. Sure, I knew it wasn’t normal for a boy to wear a dress but the way I perceived my fashion choices was similar to that one kid you knew in third grade that liked jazz when everyone else liked Van Halen.

If that makes sense.

It was… I don’t know, it was weird when I realized that male cartoon characters wearing girl clothes was supposed to be funny.

I didn’t know why at the time this was funny or meant to be funny. I realize now that this was probably related to anything feminine was meant to be hilarious or embarrassing. Essentially anything that wasn’t traditionally masculine was intended to insult or ridicule.

How did this impact us?

It was yet another nail in the “keep this side of us a secret” coffin. As if we needed another reason.

It’s a shame this side of us was ever played for laughs. How different of a world would this be if femininity was never ridiculed?

Love, Hannah

3 thoughts on “What’s So Funny About Peace, Love, and Underdressing?

  1. I’ve always found it interesting that up until around 1910 people dressed their toddlers, both boys and girls, in white eyelet pinafore dresses and left their hair to grow long and curly. Around the age of four, boys were put in pants and their hair was cut. The sense was not that toddlers were “feminine” per se, but that things we associated with adult women represented the passive subordinate role they were expected to fulfill. As psychology moved into social issues, people started to feel like this practice might be the impetus that would drive their sons to homosexuality as adults, so they started to enforce the gender binary from birth.
    I applaud modern women for rejecting this paternalistic subordination. I think that finding a better balance between the energies of both the feminine and masculine can result in a more harmonious world. Even though the feminine has been associated with women being seen as less-than, we must all cultivate it. I’m proud to express it through caring compassion and soft whimsical clothing choices.


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