On cross-dressing as narrative device

I asked for blogpost ideas recently and I got this awesome discussion question from Miramira Endevall. It reads:

There are ever so many stories about women dressing up as men to go do things, but very few the other way around, and then for comedy a la Charlie’s Aunt.

Is this because women’s spaces aren’t worth being in, or because it’s so much harder to be a woman?

As you can imagine, I had some feelings about this question.

My first gut response was a pure rejection of the idea that “women’s spaces aren’t worth being in” and so I feel like that’s a good thing to unpack. I think that perception definitely exists, especially in fantasy stories. Take A Song of Ice and Fire for example. Sansa is usually seen as the least likable of the female characters because she embodies feminine stereotypes. (I wrote a whole blogpost on this over here.) Take also many historical fantasies that are exploring very real gender inequalities where cross-dressing is usually a key plot point for female characters (such as The Lady’s Guide to Petticoats and Piracy, which I loved, or The Song of the Lioness series, which was formative for me).

But as I contemplated this question further, I started thinking about examples of men dressing as men and doing it well — not for a gag, not to demean women, but to prove they could hack it or for the joy of it. Men like Tom Holland.

You’ve probably seen the Umbrella video and if you haven’t, I recommend you go catch it. It always brings me joy, and I think that’s the case because it is a direct refutation of the idea that women’s spaces aren’t worth being in, to use Miramira’s words. Princess Jellyfish is one of the only other pieces of media I’ve seen which seems to take a similar outlook — while it is a comedy, the legitimacy of Kurako’s cross-dressing is not questioned by him or Tsukimi. It is, however, a point of conflict between him and his family — specifically, his family is concerned with politics and power, and they feel that Kurako’s cross-dressing will cause them to lose that power.

Which leads me, perhaps, to an answer: I believe that, often, gender presentation is conflated with power. That is to say, unless there is a perception that power can be gained from cross-dressing, it is not acceptable within a narrative. With books often set in patriarchal settings, it’s no surprise that tales of women cross-dressing as men in order to reap the rewards of an alternate gender presentation abound, but tales of men dressing as women are seen as deviant or exceptional.

There’s a lot more I could say on this subject, and maybe I will in the future. For now, a parting thought: cross-dressing doesn’t need to have utility in our world. It doesn’t need to be justified by power or advantage. It can just be something some people like to do, or a thing that makes you feel safer in your body, or a thing that helps you as you question whether your current gender expression is what really makes you feel whole. If you’ve got narratives of masc folks cross-dressing as women to share, please leave them in the comments.

Until next week!


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