Riki Wilchins
Op-ed: It Takes a Real Man to Wear a Cute Dress

By Riki Wilchins

Originally published on Advocate.com May 06 2014 10:20 AM ET

Yesterday, as my 7-year-old daughter and I were walking hand-in-hand shopping for a dress in sunny South Beach, she turned and said, “I don’t want to hurt your feelings,” which is usually the start of something really interesting.

I assured her she wouldn’t and she repeated, “I really don’t want to hurt your feelings. But you do look kind of unusual in a dress.”

She continued, “When you wear tights and your boots with a blouse, from the legs down you look like one person, and then from the waist up you look like another. And it’s like ‘whoa.’”

I told her I knew this and that it was OK to look different. And it was a mystery to me why this was such a big issue with people or why they cared so much about how I looked.

But of course they do. It was down here in South Beach that I last wore a nice summer dress. My partner at the time — embarrassed and stressed by all the visual attention I hardly noticed but she was unused to getting — told me if I wore a dress again she wouldn’t go out in public with me.

I was so shaken. Did I look that bad? I stopped wearing dresses for 14 years. So today was somewhat of a breakthrough. But here it was coming at me from another generation.

Becky Juro recently recounted going out for the first time dressed in feminine clothing and having some guy driving by yell “Hey, faggot!” and throw a bottle at her head. She cried with shame and fear.  

I had a similar experience my first time. As I got out of my car to cross the street, a car stopped, a guy (it’s always a guy) rolled down his window and yelled out, “You look ugly!” I too cried with shame, if not fear.

Shame is the main weapon the gender system uses to keep us in place. We are supposed to compare ourselves to cisgender women, and if we come up short — and with the amount of testosterone my particular body has had, how could it not? — we are supposed to slink away in shame or work harder to pass.

Well, I don’t pass. And it’s taken me roughly 34 years from that first encounter but I’m finally OK with looking different. I look good, if I may say so, and today that’s enough. I don’t have to look cis.

I told my daughter that I was going to wear my new dress to her elementary school, just to mess with the minds of all the kids who have told her I can’t be her “mom.”

She’s learned to laugh and say to them, “She’s transgender — deal with it!”

I’m reminded here of the Harvey Fierstein’s new play Casa Valentina, a hotel where the married male cross-dressers go to wear female clothing.

My friend Mariette Pathy Allen reminds me that it was based on the real-world Casa Susanna in the 1980s Catskills, when cross-dressers were even more hidden than today. And although they experienced a lot of pleasure and built a closeted sisterhood, they also risked jobs and families doing so, as her book Transformations: Crossdressers and Those Who Love Them documents.

The clothing and bodies of transgender people have always been heavily regulated, of course. There is punishment and hostility galore for us out there. But the shame is ours and we carry it with us, like a virus. We catch it from them, and if we’re not careful, it can infect us for decades, as it has me. Then we regulate our own selves. What a victory for them.

There was a time when I was working as a consultant on Wall Street and stepped out of the subway wearing high heels, makeup, and an expensive women’s business suit. And someone called me sir. And it stopped me in my tracks.

I’d always assumed that I was being “read,” but as a transsexual woman, which gave me some kind of entitlement to the clothes I was wearing, which made me legitimate. But what if, after all these years on the Street, everyone at every job I’d ever worked at had not read me that way?

Suppose they all thought I was a straight male cross-dresser. What if they only saw me as some kind of pervert who got off on wearing women’s clothing?

This is at a time, mind you, when I was leading very public Transexual Menace street demonstrations. And yet the idea that people might think I was a male cross-dresser literally made a cold, prickly sweat of shame break out all over my body under that expensive business suit.

I know that most of the millions and millions of American cross-dressers remain severely hidden, not to mention completely ignored by the LGBT movement. Cross-dressing is the final closet. And yet I’m constantly struck by the bravery of these men, who risk everything whenever they put on a dress.

As I explained to my daughter, it takes a real man like me to put on a cute dress and look good in it. She laughed, I made a face, and we walked on.

RIKI WILCHINS is an activist, stand-up comedian, and author of Read My Lips.