The Crossdresser’s Holiday

I often hear Halloween referred to as ‘the crossdresser’s holiday,’ in reference to the fact that it’s the one day a year when anything goes, when you can be anything or anyone you want without fear. Of course, this isn’t actually true, as any fat woman who has dressed up in anything ‘revealing’ for Halloween will tell you, as can any man who’s dressed ‘too femme’ in a hostile community, but it is true that there tends to be far more latitude when it comes to gender expression on Halloween, for people of all genders, and that makes it a holiday of particular relevance to my interests, as someone very interested in gender expression, and oppression.

I think it’s good that we have a day in the year where people can more comfortably explore their gender identities and where people have an opportunity to express their gender with less fear of reprisal. But, on the other hand, I feel like making a point of only doing this at Halloween also has the tendency to exoticise gender expression, rather than normalising it. As a result, I have mixed feelings about the day. Is it a symbol of progress, in the form of a day where people can encounter gender variance and get comfortable with it, or does it have the tendency to pigeonhole people, underscoring their ‘weirdness’ and ‘peculiarity’ by having it only really be acceptable on one day of the year?

I was thinking about this last year when I ran into a friend on the street, who looked absolutely gorgeous. She was fully decked out and spectacular, and she confessed that this is the one day a year when she gets to be the person she wants to be. The rest of the year, she goes by a different name, a different gender. This did not come as a completely earthshattering surprise to me, as I’ve picked up hints here and there, and this is a small town, where certain things tend to attract attention and discussion; it does not escape notice that her Halloween ‘costume’ is always runs along the same theme.

In her case, Halloween isn’t about crossdressing. It’s about taking the one day a year when there’s more tolerance about gender performance and personal expression, and using it to be herself. It’s not a holiday, it’s the one day a year she is allowed to simply be. She can use the name she wants, she can femme up. At the end of the night, when she hangs up her gown, she slips back into the other name and the other gender.

She’s an older transgender person, and grew up in an era when people like her were very much told that there was something ‘wrong’ with them and they ought to just toughen up and deal. I do know people in her age group who have transitioned, but there aren’t very many. She can’t be one of them, for a wide variety of reasons that aren’t my business, but I ache for her, thinking of how much she is looking forward to Halloween this year, like she does every year.

I think it would be worse to have no day at all where you could be yourself. But I also think there are some problems with calling Halloween ‘the crossdresser’s holiday,’ as it addresses only one type of variance in gender expression, and it kind of tends to suggest that other people under the trans* umbrella[1. Not all crossdressers identify as members of the trans* community, which bears noting.] should be lumped with crossdressers, which is simply not the case; trans folks on Halloween may fly under the radar by being read as crossdressers, but that’s not what they are, and it’s important for people to understand the difference between individual members of the trans* community, and to be reminded that transgender identities are complicated.

I want to live in a world where crossdressers can go out comfortably, no matter what day of the year it is, without being endangered, without attracting comments or remarks, where they can simply be accepted for who they are. And I want to live in a world where being transgender is not conflated with crossdressing, although I know some older trans folks who started out as crossdressers when they were exploring their identities, and some who are crossdressers now; these identities are not exclusive.

What do we mean, when we say that Halloween is ‘the crossdresser’s holiday’? Do we mean that it’s awesome to have a day of the year where people can be themselves? Do we mean that those people should only be allowed one day a year? Does Halloween help, or hurt, when it comes to full integration into society for people with variant gender expression and identities? These aren’t necessarily questions I have the answer to, they are just things I am thinking about, with Halloween rapidly approaching, costumes out on the shelves, pumpkins appearing on porches.

It will always be a kind of bittersweet holiday for me, I suspect, because there’s something that makes me very sad about people who can only be free, who can only live, one day a year. Because at the end of the night, some of us have to put their identities in boxes and get ready to square off against the world on All Soul’s Day with the memories of being themselves receding in the background; how long can you hold on to that? A year? I know I wouldn’t be satisfied with only being allowed to be myself once a year, with the knowledge that when I was, it was as an object of fun and mockery.