Crossdressing Advice From Bart Simpson

Haven’t done any crossdressing comics for a while, so here’s one from the Simpsons episode “Bart’s New Friend”

At school the kids are organizing a game of tag that involves players crawling between one another’s legs. Milhouse looks down and observes sadly, “I guess I chose the wrong day to wear culottes.”

Every day's the wrong day to wear culottes

Every day’s the wrong day to wear culottes

I agree with Bart’s response: EVERY day is the wrong day to wear culottes. If you’re going to wear something that looks like a skirt, just wear a skirt! Although it looks from this picture like Milhouse was indeed wearing a nice pleated regular skirt, rather than culottes. Get your fashion terminology right, Simpsons writers!

This isn’t the first time they made that mistake: Way back in the episode “Two Dozen and One Greyhounds”, Bart explained that he was out of clean socks and had to wear some of his sister’s to school.  Homer angrily confronts him: “How do you explain the culottes, boy?”  “I had to coordinate, didn’t I?”

I guess Bart’s position on culottes has changed. Maybe he learned a bitter lesson that day.

About Ralph

Male. Straight. Married.
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2 Responses to Crossdressing Advice From Bart Simpson

  1. Vivienne says:

    Hi Ralph. I suppose a social commentary as wide-ranging as The Simpsons would inevitably cover crossdressing, sooner or later.

    I was thinking about how, statistically, at least one male in Springfield is a crossdresser. Who do you suppose it is? Ned Flanders? Mr Burns? Smithers? Sideshow Bob? Kent Brockman? Willy the Janitor (Och aye!)? Apu? Moe?

    The problem is that each of these characters is dysfunctional in some way (as everyone in the show is) which means that if _any_ of them were shown to be a crossdresser, there would be someone in our (real) society who would draw parallels between the deliberately odd traits of the character and the supposed odd traits which we all “know” crossdressers possess.

    So I guess there are no “wholesome” crossdressers in Springfield! Unless you know different!


  2. Ralph says:

    Well, you could argue that the residents of Springfield (crossdressing or not) are flawed, just like those of us who arguably exist in the real world.

    Someone did an excellent roundup of the various ways the Simpsons writers have introduced fodder for discussions about sexuality and gender — often just as a throwaway joke, but sometimes with that “ha-ha, only serious” thought-provoking social commentary that is the reason I love the writing so much. The 15th entry on the list answers your question, with examples of the many times over the years various characters have gone femme (or at least drag):

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