Chiffon. Taffeta. Tulle. Satin. Silk. Velvet. Lace. These are the seven deadly fashion sins of cis gendered men. One exception, Hugh Hefner and those fabulous silk jammies. Ed Hardy t-shirts might be in the sinful Top 10, but that’s another topic altogether.

How did we become a society where certain fabrics and cuts of clothing are off limits to half the population? A woman can wear a suit & tie and it’s considered chic. A dude puts on a tulle skirt and the townsfolk rush the Pitchfork & Torch aisle at Home Depot.

I should know. I’m a dude. I’ve been writing music editorial for Popdose for five years. I love 80’s new wave, 70’s punk, and long flowing skirts from the 1860’s. But for most people, that latter one is a forbidden love.

Please note how I do not refer to myself as a trans woman — yet. I have befriended many wonderful trans women, we share many similarities in terms of background, experiences and identity; but we also have many differences. I am not entirely sure if my journey will include hormone treatment and surgery to properly align the soul and the body. For many of my trans friends, they enthusiastically moved forward without ever having a doubt. Like many people elsewhere on the gender spectrum, I have doubts, fears and questions that need answers. This is the journey I will document here. 

Last summer, without a trace of makeup, I walked hand in hand with my wife on a summer day, wearing a Foo Fighters t-shirt, a floor length chiffon maxi skirt and flip flops. We live in the progressive sanctuary of Seattle and still I got assaulted with snickers, guffaws, and of course, quips like these:

”Faggot!”

”That’s not a kilt!”

”Cut your dick off yet?”

”Pick a side already!”

The barbs don’t only come from men. Ironically, many of the women who called me out for “cross-dressing” were wearing Seahawks jerseys — and not the cute, girly cut, fitted tops; those giant, bulky, Official NFL ones with the names of the male players on the back.

After staying silent about my gender identity for most of my life, I finally went public in the summer of 2015. At the time I thought I was trans, but some people told me I was just a crossdresser. The latter certainly isn’t being celebrated in the pages of Time and EW or on Amazon TV.

As I began to move through the year, finally exploring what may or may not be an authentic expression, I got a taste for what women have been going through for generations: the pressure to be magazine flawless, how they must diet and jazzercise their way into trending fashion instead finding clothes that simply look fabulous on their natural bodies. It was women who gave men the “dad bods are sexy” exemption, why not take a similar one for their own team? And cis women are not alone, in the age of Caitlyn Jenner, their trans sisters are under pressure too — to be 100% passable, 100% of the time as if gender was an all or nothing sport. I too grew embarrassed to be seen in a dress without makeup — and Photoshop.

The anger I received in public was jarring, I began to make up my own theories. Perhaps some men’s reactions to me in “women’s clothing” might just be a reflection of their own feelings about women — if they think women wear sexy clothes solely to be sexually desirable to men; then that must be my intention too. If women are only perceived to be sex objects, then anyone wearing women’s clothes must be filtered through the same lens — which makes some men confused and angry.

From birth, boys are told to “man up” and “show some balls” as if bravery is for men and men alone. Femininity is viewed by many men — even some feminists — as a weakness, society’s way of putting women on pedestals, trophies on display. Look no further than red carpet coverage at any awards ceremony. Men get paid more. Women get criticized more. Women can run for President, men get elected. Why would any one in the power group voluntarily join the other team?

A little makeup, photoshop and Hollywood magic

I love femininity. It flows through me. It empowers my creativity. Gender is about much more than clothing, but for gender non-conformists, clothes are constantly in the crosshairs — in the media and from random strangers on the street. When a man shows the slightest trace of femininity, clothes take the first hit, body parts take the rest. Nobody ever asks about how you feel. All they care about is how they feel, and most of the time that’s angry, afraid or disgusted. But why?

Stepping outside gender lines turns transitioning women or feminized males into lightning rods to absorb other people’s shame and insecurities. When it comes to men wearing pink, for many, there is no grey area. The gay population has been dealing with this for generations too — show me a homophobe and I’ll show you someone with unresolved homosexual urges. People who are grounded with their sexuality and gender identity tend to have a ”live and let live” mentality. People who are unsure on these fronts act out on fear, turning shame into hatred, letting the darkness of ignorance lock the potential joy of enlightenment in the closet.

I can’t speak to the full spectrum of struggles faced by trans women because I am not one, but still, I struggled to figure out why some people are genuinely scared at the thought of a man wearing a dress? If we’re wearing heels, we couldn’t chase you if we tried. If you’re a dude and you check out a hot pair of legs and roll your gaze up a sexy dress only to realize that dress is wrapped around a trans woman, a drag queen or a man, it doesn’t mean you’re suddenly gay. You were already gay, bi, straight or somewhere in between before you saw them. Once you realize who they are, if you’re still attracted to them, then you’ve just learned something fabulous about yourself. If you simply move on and say to yourself, “oh, good for them” then congratulations, you are a sensible and grounded person.

I love the phrase, ”Sexuality defines who you go to bed with; gender defines who you go to bed as.” It dispels a lot of confusion in a single breath. This is bad news for politicians who want to use trans people or people like me to scare and distract their base while they raid the treasury and systematically dismantle civil rights. Trans women and non-binary people can only distract voters if they’re perceived as deviants, perverts and pedophiles. Hate to break it to you, Depeche Mode was right, people are people. Some people are just braver than others to express their desires and truths without shame.

Gender Nation X has one purpose: to make it less jarring the next time you cross paths with a transgender woman, a gender nonconforming person, or a man in a dress. There are plenty of blogs, websites and media platforms addressing trans issues on all fronts, my intention is to add to the conversation, not define it or pull focus. Everyone has a story and a perspective; this is just one ray in the rainbow.

Twice a month, I will share my stories from my 40 year struggle to find my home on the gender spectrum — some might make you cry, some might make you laugh, all of them I hope will inspire. One thing that gets lost in much of the media coverage on trans issues is the pure joy that comes with finally realizing your true gender expression. There’s humor to be found in trying things on, seeing what works and what definitely doesn’t; finding a dress you can zip into and safely exhale without ripping it to sheds like the Incredible Hulk. There’s fear too. I am scared shitless of being authentic in a world where Trump has energized bigots faster than radiated atoms.

2017 is going to be a huge year — I will document every step of my journey here. Learning makeup. Shopping online and in stores. Stepping into a world where hated and violence go hand in hand.

Connect with Gender Nation X on our Facebook Group. Share your story or send comments to me here.

Until next time, stay true to your beautiful, fabulous self.

Huge thanks to Tania Zimmer Photography for the B&W cover image and Lena Eivy Photography for the “Free Your Mind” portrait. These photo sessions have been a huge part of my journey, I will share tales and more images in upcoming posts.

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About the Author

Keith Creighton

Keith is a music correspondent for Popdose and an advocate on women's empowerment, gender identity, and gender liberation issues. He is a monthly new-music contributor to the Planet LP Podcast and is a marketing writer by day for Sudden Monkey.

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