Unsex me now

I have Halloween issues.

Poignant memories of costumes gone horribly awry haunt me, relieved only by the certainty that few pictures survive. I keep one or two tucked away as a reminder, a warning.

But I also treasure moments of commune with someone else’s clothing, and the memorable times when the costume worked. Since I was big enough to open the tickle trunk by myself, dressing up and traipsing about has been a fond yet generally closeted pastime – with the exception of Halloween.

When October comes around again, we all get another kick at the can.

This is a good thing, because we still love dressing up don’t we? Whether it’s the spontaneous, the habitual or the semi-annual version? It’s the great equalizer, the night where everyone has a free pass to create the most outlandish, unexpected version of themselves.

It’s a big responsibility.

So I’ve set myself a daunting task this year: I’m going to make me a man. Or a boy. Or a reasonable facsimile thereof. Halloween isn’t necessarily about gender subversion, but it’s a damn good excuse to give it a whirl.

There’s a reason that drag is homosexuality’s surprise cross-over hit.

Ever notice that the most dyed in the wool macho guy is the first one to slip into a dress and heels when it’s costume time? Can you remember your butch cousin Brad saying “and I was looking damn fine too!” when he showed you the picture?

It’s a startling freedom to be able to change both your perspective and your image just by tying a Windsor knot or pulling on some pantyhose – a freedom that is incredibly sexy, and damn hard to regulate. If it was easy, Speedos would be licensed and frills would require training.

Literature is liberally peppered with plots entirely dependent upon the confusion generated by masquerade holidays and cross-dressing. Is it any wonder drag is still considered risqué in some circles when it opens up the possibility of Olivia falling in love with Caesario, and the maid is no longer always a maid? Some people genuinely fear this kind of error.

Whether for personal expression or civil disobedience, dress has been designed, dictated, imposed and disposed of. But the more someone tells us what to wear, the more we seem compelled to do it our own way. Repression only begets reprisals, and today, the single most effective way to swing the pendulum continues to be the bending of gender. Drag can be quite tastefully subversive when carried well.

The art of course is in carrying it well.

Part of the problem is the pressure when it’s a once a year proposition. If things go awry, you have to wait a whole year for redemption. Another problem is commitment – understanding the rich history of drag, and taking the time to learn to walk in heels or perfect the distinctive stride of the male of the species.

Mostly, it’s a question of knowing what to wear.

Some say the term “drag” comes from the theatre. During a time when all roles were routinely performed by men, cross-dressing parts were known as “drag roles” because of the difficulty of acting convincingly while managing long skirts dragging across floorboards.

This is the central problem for the amateur cross-dresser: gender-specific clothing is just plain weird, and damn hard to manage when you don’t know what you’re doing. Add to this the complications involved in the display of sexual characteristics – whether you stuff or pack – and you have a recipe for costume disaster.

But I have a plan. Since October is gay history month as well as Halloween, I’m going to take my costume cues from one of the many women who had the temerity – and the tailoring skills – to pull off drag on a grand scale.

I’m going to dress as a woman who lived as a man.

Think about it – finally my persistently feminine secondary sexual characteristics will not be working against me.

The only problem is narrowing down the choices. It’s amazing how many women have pulled off life as a man. Take Charlotte Darkey Parkhurst (1812-1879), aka Charley Darkey Parkhurst, who escaped from a New Hampshire orphanage and found work as a boy in a livery stable. She learned to drive a coach, and eventually became “Mountain Charley,” one of the greatest stagecoach drivers of the old west.

Mountain Charley died of tongue cancer, some say because she held her tongue for so many years.

Now that’s subversive. All I need now are some chaps.