Men Who Dress Like Women

Friends, finally, the topic you've all been waiting for.  Isn't it time we addressed the 10-ton elephant in the room?  And what better time than MPB Guy Week?

Grab a cup of coffee, turn off the radio, and shut the door -- I have a confession to make. 



You know how in books,  movies, and sit-coms like The Prince and the Pauper, The Parent Trap, Dead Ringer, and The Patty Duke Show, there are always those moments when the identical cousins, or twins, or what have you, will switch places to play a trick on everyone else -- usually the high point of the story?

Well, my beloved cousin Cathy and I....oh, dear, here goes....sometimes we do the same thing and we've been doing it for years!  I'll even share this: in more than one of the more than dozen Cathy photo shoots you've seen here on MPB, you're actually seeing me and not my cousin Cathy.

I bet you'd never have guessed.  That's because we look so much alike!



(I remember once receiving a comment to the effect that, Cathy looks like she's having a bit of a 5 o'clock shadow problem, and it was all I could do not to blurt out, You fool -- that's me!   But of course I didn't.)



In any case, let's talk a little about this.  A lot of people are probably wondering:  What on earth would possess a man to dress up like a woman?

Friends, there are two kinds of men: men who occasionally enjoy dressing up like a woman, and men who would enjoy it if they ever gave themselves the chance.  There are a few other kinds of men too but we can't possibly cover everybody today.

In any case, I think if you men were to ask yourselves -- and you women were to ask the men in your lives -- if they'd ever put on a brassiere, lipstick, or a pair of pantyhose (not necessarily at the same time) the answer would be 100% affirmative.

Rest assured, the ones who are denying it are simply not telling you the truth, likely out of fear of condemnation.  I'd wager that whenever they find themselves safely home alone for more than an hour or two they're rifling around in your makeup kit or trying on your Christian Louboutins. 

But why?, you ask.

Because it's 1) fascinating, and 2) fun!

Have you ever been in a play?  Have you ever experienced the thrill of pretending to be someone else, of putting on a costume and making yourself look (and feel) different?  And if you were actually good at it and elicited a positive response in others, you know it was doubly thrilling.

Men dressing up like women -- cross-dressing, as it were -- has a long and celebrated history, stretching back to the days when women were not allowed to perform on the stage (and probably before).   Women have been dressing like men equally as long, but for too many reasons to go into here, it never seems to have the same power or impact on an audience (says me).

There is something about seeing a man dressed as a woman, say Flip Wilson as Geraldine (above) that packs an emotional wallop you don't get from Lucy dressing like Harpo Marx or Ragtime Cowboy Joe, though neither Flip nor Lucy is especially convincing.

I have always loved watching men impersonate women, and some of the best, like Charles Pierce and Jim Bailey, were often guests on popular variety shows like The Carol Burnett Show.  (Flip Wilson, of course, had a show all his own).  Today's fantastic drag performers have fewer mainstream venues and why this is could be a blog entry all its own.  Sure, there's Ru Paul, but the media landscape is much more fragmented than it was forty years ago.

Which brings me to the final point: male-to-female drag or "gender illusion" as it's sometimes called, can make some people very uncomfortable in a way that a man dressing like a clown does not.  Why, do you think, are there still so many people who don't want to see the lines blurred, or crossed, or what have you, and would punish severely any (male, it's always the male) child of theirs they caught dressing up like a girl?

If a boy likes to dress like a girl, or vice versa, why is this a problem for anybody?  It's not for the boy or girl; it's the soul-crushing social stigma attached that causes the pain and confusion.

I hope that if you have a cousin Cathy you like to dress up as, you will do everything you can to make your Cathy side welcome and cherished in your lives.  Emotional health and happiness comes from embracing everything you are and celebrating it fully; anything less results in frustration, depression, and worse still --projected self-loathing onto others.

Gender identity is too rich a topic to distill into a short blog post but rest assured it's both more varied and more benign than many would have us believe.

It doesn't have anything to do with who we are in our hearts and the positive contributions we can make to the world.

Go for it!