I am a cisgender, gay man who often wears women’s clothes. I’m neither a drag queen, nor am I trans. I just really, really like fashion and gender-bending.
When I was only a few years old, I had a fascination with a pair of silver heels that my mother had in her closet but rarely ever wore — and let’s be honest, even in the 90s, it was probably better that she didn’t wear them. At the time it was easy enough for my mother to rationalize my obsession with her footwear: I had a VHS copy of Disney’s animated Cinderella that I watched on a loop, and the silver heels reminded me of Cinderella’s own glass slippers. I was a child who was obsessed with the idea of magic in its many shapes and forms, and those shoes were the closest manifestation of magic that I had in the house. After all, it wasn’t as if my Southern Baptist mother kept magic wands or cauldrons lying around.
Though my family let me play out my make-believe, I’ve had relatives since then tell me they knew that I was gay going back as far as to the time of those silver shoes. But back then I was just a child who didn’t have a father with no real knowledge of gender norms that had predominantly been raised by his mother and grandmother, save for the occasional stepfather. Although, as I got older, my infatuation with clothing that wasn’t made for boys only increased. In line with my magical obsessions, when friends and I would act out scenes from movies or TV shows — let’s take Sleeping Beauty as an example — I would drape myself in cloak-like sheets to personify characters such as the villainess Maleficent. That was just the kid I was. I was obsessed with witches, and as an adult now I can understand that better, but will save that rationale for another essay. But this activity bled over into my teenage and adult lives. I grew my hair out to chin and then shoulder-length in middle school, chose flowing Halloween costumes I thought were cute, and even began to design — albeit, quite poorly — clothing I thought might suit me better than the choices boys were given.
It wasn’t until over a year after I came out in my early twenties that I started playing seriously with clothing that was a little more gender-neutral followed by choices that were unmistakably gender-bending. Now, it took quite a long time for me to get comfortable enough with my body to be able to wear these items of clothing and feel comfortable doing so. After all, a lot of them left parts of my arms, chest, back, stomach, shoulders, back, and legs exposed that clothing considered to be “male” normally would not. But when I started to find clothing that looked good on my body and that celebrated it in a way that I felt my body should be celebrated, I never even once thought about not giving myself the option to do so. I began wearing tops with V-necks that cut down just above my belly button. I found the comfort that could be provided by a pair of leggings under a long shirt. I enjoyed the flow of a skirt and the sexiness of a midriff top and the appeal of makeup and the fun accents of scarves, shawls, and jewelry. Hell, I even wore a dress and shaved my legs to perform in a show back in October — although the dress had more to do with the fact that I was singing “Defying Gravity” from Wicked. What I found as I wore these things was that I wasn’t just playing dress-up as a kid anymore. I was making a statement about my who Anthony was as a person.
That’s where things began to get tricky though. The more that I made the conscious choice to bend the rules of what was socially acceptable to wear for men in an effort to express myself, the more people struggled to understand my identity. Even just as recent as two weeks ago while at a concert with my best friend in Dallas, a gay couple I’d bummed a cigarette off of asked me if I was a trans woman, as I was wearing high-waisted, black, skinny jeans, a green top tied in the front to expose my mid-section just a bit, a full face of make-up, and my favorite black matte lipstick. My friend — who teases me about everything — found this to be funny, but by this point I’d gotten to a place where I was used to it.
You see, in the past I might have been made uncomfortable by such questions, simply because I was fearful that I was presenting as a female and that people would have some sort of adverse reaction to that or that they wouldn’t be able to accept the fact that I am anatomically male and that I identify as such. I was neither upset nor was I offended for being confused for a trans person. I was afraid of being confused for a trans person, because as much as I was expressing my identity through my clothing, my clothing was not just an expression of my identity, not a definition. After all, the gender norms associated with clothing are a societal construct; they grasp no bearing on my identity. I was and continue to be a person who constructs their own rules and likes to turn heads. I’m a cisgender, gay man — plain and simple. Do I gender-bend with my clothing? Hell yeah. Am I drag queen? Noooope. In fact, I’ve never even had the slightest interest in performing as a drag queen. And that’s just the thing: I’ve never wanted to be, nor have I ever felt like I am anything other than a boy. I’ve never felt that I was born in the wrong anatomical body and I’ve never believed myself to be a woman. I’m just a gay guy who loves the look and feel of clothes that are typically manufactured for women and who thinks that it’s bullshit that we live in a society so contaminated with dangerous gender norms that we can’t wear certain colors or designs or fabrics.
As a kid and well into adulthood, I struggled with my weight. I had issues with my body, although not ones that extended to my genitalia. Trust me, I love that part. But as a teenager, I always struggled with feeling fat and I worried about what clothes and haircuts made me look like through the eyes of others. Throughout my last three years of high school, I suffered from bulimia nervosa, and in my final year, I got so addicted to weighing myself that I was running seven miles in the morning before school and seven miles at night before bed. And while that might seem to be a silly thing to worry about, it was a very real thing for me. As an extension, the clothes that were made for young men weren’t well-suited for my body. But even as I’ve become more comfortable and confident with my body, I don’t find that “masculine” clothing always makes me feel attractive. Sometimes it does, other times it doesn’t. Although, I’ll be the first to admit, my problem stems from an even larger social ideology about what is and is not perceived to be attractive. Still, I’m human; and a part of the human condition — at least, I believe — is to want to be desired by others and to feel attractive.
Now, I don’t wear strictly clothing made for women. I wear a lot of different articles of apparel made for a lot of different people, and that’s really only because I absolutely love fashion. Most of my favorite outfit combinations are those that mix-and-match clothes that you wouldn’t find in the same department or section of a store. For instance, just last night I wore a pair of black leggings over a very low-cut, black V-neck with a large, elastic, black belt around my waist, my long, brown hair pulled back in a ponytail, green lipstick, and a pair of black, men’s dress shoes. And let me tell you, henny, I looked real good. So good, in fact, that I wore the same outfit again tonight to a different event. But the point of me wearing it isn’t about me identifying as male or female, as clothing throughout the ages has shifted and bent to what is considered “male” or “female” or “neutral” or whatever. My experience with fashion is about me expressing not my gender identity, but my personality. And, if anything, I’m identifying myself as a person who is confident enough to wear whatever the fuck he wants, so long as it’s something that makes himself feel sexy and classy and sometimes — if I’ve had enough tequila shots — even a little slutty.
I’m a dude. My pronouns are he/him/his. I love drag queens, and I love my trans and nonbinary siblings in the queer community. We’re just different in this way. Sure, my friends and I all call each other ‘she’, and sure I’m going to get mistaken for being a trans or nonbinary person probably for the rest of my life; and I’m perfectly okay with that. Certainly I will not wear a tux to my wedding when and if some poor man ever decides that he’s not going to do any better than a loud-mouthed, alcoholic kvetch with a mild drug problem who says whatever he wants whenever he wants and eats way too much pasta. But I’m still a guy; and while I believe that gender is a very broad spectrum and I am vehemently in support of my trans brothers and sisters and nonbinary siblings, being a gay man is an important part of my identity — just as correctly gendering trans and nonbinary people is an important part of theirs. If you mistake me for a woman or for a trans person or for someone who’s nonbinary, I’m not going to be upset about it. Recently, I’ve even begun to laugh about it, simply because it’s kind of refreshing to know that we’re slowly getting to a place in history where more and more people are comfortable asking your pronouns so that they don’t upset you. But I will politely remind you that I am a cisgender, gay male who just so happens to sometimes wear tops targeted toward and sold to women because I know what I look hot in. But more importantly, because I feel hot in them. And based solely upon the number of men who asked me for my phone number last night, I’d say it’s not all in my head.
I say all of this not to go on the defensive. I don’t care about that. I’ll answer to pretty much anything except ‘sober’. Again, it’s encouraging to know that more and more people are becoming conscientious of gender identity and are wanting to affirm the genders of others to include them in the canvas of society. I say these things because I know there is probably someone else out there who grew up wearing his mother’s silver heels after watching Cinderella on a loop that got teased or made fun of that isn’t quite where I am in terms of feeling comfortable in skin and clothing. And to those little boys (or to the little girls in vice versa or however it may apply to anyone), I say this:
Wear what makes you feel good, and let that goodness blossom into confidence. Not that it matters what other people think, but if you feel sexy, chances are that other people will find you sexy, too. Appeal isn’t really about what you’re wearing or how your makeup is done or if you had time to get your hair curled or your nails painted. It’s about exerting confidence in how you look and showing other people that you don’t care whether or not they like it so long as you do. And that’s the real key to sexiness — not in the eyes of others, but in those of yourself: confidence.
And as a sex columnist and a Grade A Snacc, I know a thing or two about what’s sexy; and it’s in all of us. You just have to make sure that it feels right to you. Nothing else matters.