It Doesn’t Matter What Kind of Horse you Ride in on, Baby, You’re Still a Cowboy.


Caitlyn Jenner sure opened a can of gender-blending conversation bait this week.

As for me, It’s another night at work, and I’m pouring drinks for boozed up, tarted up, cross-dressing fedora’d party boys and girls in a scandalously dark Hollywood bar.

Leggy boys in black vinyl pencil skirts and major size 12 heels teeter and lean on the bar where citrus drinks called “Skinny Bitch” are on special. And I’m thinking, God, those getaway sticks are long.

Not so easy is it, my friend, walking in those stilettos?

“Julie” asks me if she’s wearing too much Chanel Number 5 (she is), but I’m too preoccupied with worry over her knee joints. “Be careful in those things,” I say, like I wasn’t inappropriately wearing 5” tall thigh high leopard boots at a BBQ last weekend.

I think Mad Max somehow got it on with the Black Swan, after which she laid a bunch of eggs when a lightning bolt sashayed down from the heavens to the tune of David Bowie’s “Life on Mars” and struck the nest, which ended up bursting into a mosh pit of flames and glitter and out came these night crawlers, subculturists and sexual free spirits in corsets on a Friday night, ready to disco down.

Now I know where the wild things are.

While crossing the “traditional” lines of gender—or blending them—is about more than just a costume change and Revlon Red lipstick, what’s curious is the desire to look and dress like something one could never really be—the opposite sex. Joan of Arc. Elton John. Mrs. Doubtfire. People had a fit when Katherine Hepburn was seen wearing—gasp—pants in public, until they started copying her. There’s nothing new about questionable gender identity, but the chatter has, it seems, come to a fever pitch.

I admit: ever since I saw Brian de Palma’s Dressed to Kill, I’ve had a bit of fear of men in drag. And psych hospitals. What can I say? I was 14 years old.

My next door neighbor shoots trans porn. Watch what happens when I rearrange the words: my neighbor shoots trans porn next door. Tall people come and go, and some nights I can hear them whooping it up poolside on the other side of my fence.

What’s to fear? They seem so happy, so well adjusted; only super happy people laugh like that at the top of their lungs.

It’s 11:30 at night. I can hear at least four of them next door right now in the jacuzzi, in some kind of tequila-fueled, cackling uproar. I’m dying to know what’s so funny.

I met one fun-loving person outside the house the other day. At 6’4” in sneakers, she was even taller close up.

“Hi! I’m Roxy!” She had the cutest freckles I’ve ever seen.

We shook hands. Do girls do that? Or only men? Or men and women? Hell if I know…With so many options, including the fist bump, the “bro” hug and the European double cheek kiss-kiss, I’m briefly confused. I almost blurted out “girl power!”

Roxy’s height is hardly a disadvantage; I have a theory that people of stature are more successful in life because they so easily intimidate others. Clint Eastwood is 6’4”. Who’s going to say no to someone who makes you feel like a Lilliputian? But I figure Roxy’s had her entire adult life to get used to towering over people, and that her tallness has been the least of her problems in life. Still, I wonder if it bothers her, now that he’s a she.

So at 11:30pm, I decide to go knock on the my neighbor’s door to talk to Roxy. My husband tries to stop me.“They’re drunk,” I say. “This is perfect.” Besides, I had just run into her that morning at the Coffee Bean & Tea Leaf, where I saw her tallness over by the creamers and the honey sticks.

To sum up an hour of chit chat: Roxy is very clear about the fact that she is living outwardly as a woman, by perception, and is very proud to be transgendered—but not an actual female.

“I’m not projecting myself to be anything other than a transgendered woman. I know what it’s like to be on hormones, and not be on hormones—there’s a big difference. I don’t know what it’s like to menstruate. I identify as a female, it says female on my license, but if you want to know about my gender, I’m a transexual. I say this all the time: If you have two dalmatians, and one day you bring home a little black lab puppy, it’ll do everything the dalmatians do, and it’ll try to be just like them. But at the end of the day, it’s still a black lab. And that doesn’t make it any less of a wonderful pet. You can still be the best you.”

I believe there are two kinds of people.

There are the searchers, the artists and dreamers and poets who dare to live with open hearts and be whoever they want to be despite what others think.

And then there are the people who fear them, afraid of change, the censors, the activists who work to deny certain freedoms to certain individuals. When Tipper Gore started slapping “Parental Advisory” warning stickers on 2 Live Crew albums, I’m pretty sure no one really had the impression they were buying a collection of lullabys to begin with.

What is so wrong with just letting things be?

A rock can’t stop the flow of a river from finding it’s way; it’ll make it’s way over and around without effort. Be brave, and be the best, most unstoppable you.

Because no matter what kind of horse you ride in on, baby, you’re still a cowboy.

As a former girl-on-the-loose myself, my friend and I once got ourselves kicked out of a midnight showing of The Rocky Horror Picture Show for smoking in the theater. But not before the sweet transvestite Dr. Frank-N-Furter came prancing onto the screen like a ferocious, uber-sexualized cross between Danny Zuko and Cruella De Vil.

Seriously, has there ever been a male movie character in a dress—besides Tootsie—who didn’t break out into song and dance or go on a killing rampage? No wonder there’s so much confusion and misunderstanding.

Corseted and feathered. All man. Like a modern day goth champion of authenticity, the kind that might not be everyone’s version of truth, but maybe what the Roxys of the world desire, as well as all the nonconformists, the quasi-deviants, the questioners, the brave souls and the lonely hearts.

The fact is, they actually do make those stiletto’s in a men’s size 12. You can get them on Hollywood Blvd, near the Chinese Theater and the fancy new American Apparel. And no, they’re definitely not easy for men to walk in while they try to shake their ass.

Keep practicing, darlin’. It gets easier.

Could this be the last laugh for the female species? If so, let’s all laugh together. It’s so much more fun.

Originally posted on elephant journal June 6th, 2015


Written by Anne Clendening
Anne Clendening was born and raised in L.A. She's a yoga teacher, a writer and occasionally slings cocktails in a Hollywood bar. She could eat chocolate cake for every meal of the day. She has a huge fear of heights and flying. And fire. She wishes she could speak French, play her guitar better and make cannoli. She's probably listening to The Dark Side Of The Moon right now, kickin’ it with her boxer dog and her hot Australian husband ★