Yes, I'm Wearing a Dress to My Own Wedding
How my engagement revealed the gap between political correctness and genuine understanding
It’s interesting how everyone claims to “get it” when the stakes are low. But when you raise the stakes a bit, you see just how disconnected they really are.
Perhaps this is why silent respect forms the bedrock of a broken society. To a degree, it’s necessary; we all judge in silence and value a semblance of “live and let live.”
But that silence holds us back. Many get lost looking for the sweet spot between respectfully drifting away and thoughtfully engaging in an effort to truly understand. There is an equilibrium somewhere in the middle; a nuanced state where one says, “I’m not against your right to express yourself, but you need to go a little deeper so I can actually empathize.”
But getting there requires vulnerability and the risk of offense on both sides. It requires a bold foray into the conversational unknown, a territory that can only be navigated with inquiries and vocabulary that haven’t been pre-approved by HR.
To truly understand means encountering discomfort and trudging forward nonetheless.
I’ve been crossdressing full-time, public and private, since 2020. Five years of collecting gawks and scoffs as a man in heels turns confused heads looking for the right pronouns. I barely even notice it anymore.
About two years ago I was in Vietnam on a work trip, walking down the main strip in Saigon with a coworker who mentioned that every single person was staring at us.
“That’s because it’s 100 degrees outside and I’m sweating my tits off,” I retorted, attempting to break the tension created from wearing a sports bra as a top in a foreign country.
“No, but for real, that’s my bad bro,” I continued, newly accustomed to apologizing for what feels like public baggage any time I go out in public with another man.
When dressed “normal,” two dudes grabbing a burger is about as standard as it gets. Have a few beers, talk about chicks, blow off some steam. No one thinks twice.
Take those same two men, in the same exact circumstance, except put one of them in a dress. The difference is staggering. All in the name of acceptance and progressivism, the gears start turning and assumptions fly.
“Congratulations! You two are adorable!” they’ll say if either of you just happens to order a dessert, assuming it’s another gay holiday they haven’t heard of but need to blindly support.
True friends are always nice about it and reject the apology. They usually seem to enjoy the front-row seat to the nonsensical social circus, especially those who knew me before. But I still apologize anyway.
Regardless of whether it’s fair or not, I do, in fact, bring baggage to the social dynamic. There’s no denying it. If your goal is to blend in entirely and be the least noticeable person in the room, going on a date with me is a living hell.
And I’m not without empathy for that perspective. Crossdressing is weird. It is objectively abnormal, beyond the scope of what most people think about. I didn’t choose to feel this way; I just do.
When people ask me why I like lady clothes instead of man clothes, I usually describe it like a favorite color.
“What’s your favorite color?” I lead, with my next question already prepared, regardless of how they answer.
“Okay. Why?”
Usually they pause, worried it’s some kind of trick. “Why is it your favorite color?”
That’s when you get to see that magical moment of brain neurons firing, followed by a pretzeled brow unaccustomed to such introspective self-inquiry. It’s a phenomenon not uncommon for those in the luxurious position of fitting into a normal box, welcomed by the dregs of society.
They have yet to realize there is no why.
“Don’t worry,” I always follow up. “I don’t know either. All I know is that when I wake up and look in the mirror, I want to like the person looking back. I can’t explain it specifically, but I just prefer things that are cute, pink, and femme.”
If they return too blank of a stare, my last-ditch effort is to meet them where they are and borrow a term from The Matrix that analogizes it perfectly:
“My residual self-image is more like Trinity than Neo.”
These conversations are nothing new for me, though I’m happy to keep having them. When you are the black sheep, it’s important not to be hypersensitive or angry at your genetic dice roll. You are what you are, and getting mad about it isn’t going to make it better. Release that anger, get square with your creator, and do the only thing we can do with our limited time here: survive. And if you’re lucky, thrive.
I expect the confusion from strangers.
However, I thought we crossed these bridges long ago when it comes to friends and family. Yet five years later, we’re still mulching over the same shit.
“What will you wear during the proposal?” I heard when retrieving the family ring for our engagement, understanding fully it was coded language for: Will you be wearing a dress when you propose?
What a strange proposition. Could you imagine proposing to the love of your life, asking for her hand in marriage, committing to a contract with cosmic consequences, and basing it on a lie about my outward identity?
You know I have to look at the engagement photos too, right?
How could I call someone my soulmate if I have to hide the loudest part of myself to secure her commitment?
It just doesn’t compute for me. And unfortunately, it signals an all-too-common notion that my crossdressing is just another phase; another plea for attention that will fade away like my interest in playing soccer or learning guitar as a youth.
And that’s when I feel the frustration boil.
Coming out was no easy task. I was always expressively ‘different,’ and even in high school remarked with loud jealousy of my female friends’ ability to wear comfortable, flattering fashion. As a kid, I was picky about clothes and hated dressing up in any kind of formal attire. It took me decades to realize that was a form of self-repression; I didn’t have the vocabulary or confidence to say I wanted to wear women’s clothes. It didn’t feel like I actually had a choice as a kid in the 90s. I just did what I was ‘supposed’ to do.
That all changed in the decades to come, especially in the post-Me Too era. In those days I was still working as full-time broadcast talent and was simply afraid that going public would hurt my career. I was nervous that my already tight cash flow would be cut off and, even worse being mocked online—I’d have to get a real job instead of talking about video games all day.
So I continued to stuff it down and leaned into THC as an effective coping mechanism.
But then, after a long series of circumstances, I touched a rock bottom and that fear suddenly wasn’t so scary. For the first time in a long time, it felt like I didn’t have much to lose. And if that were truly the case, there was no sense in hiding any longer.
I ordered my first dress on Amazon: a simple, sleeveless, black fit-n-flare skater dress. The day it arrived I waited anxiously until the night hours, when my roommates were asleep, before tossing it on and taking a long stroll around the neighborhood. No one saw me, but it was a strangely exhilarating feeling.
It felt like alignment.
When I got back from my walk, my roommates had gotten up and were in the living room as I opened the door, completely unaware of what they were about to see. They both paused for a second, mouths open almost touching the floor, before shaking it off and attempting to pretend it was just another day.
“Dude, rockin’ the dress!!” said one of them, in a genuinely excited tone.
“Yeah, I decided to try it out and go for a spin. This might be me now,” I said, still buzzing from the emotional whirlwind of my first public debut.
“Shit, it’s about time,” he continued, as we laughed and reminisced about some of my previous fashion choices.
My other roommate wasn’t actually that surprised, just caught off guard. Both remarked that they saw this coming for a while and were overall happy for me that I didn’t have to hide any longer.
And weirdly, I felt stupid. I was mad at myself for being scared of how two of my closest friends would react. I also felt stupid for building up this big reveal in my head, knowing full well that I had been using a women’s wallet, carrying purses, wearing leggings, and idolizing Carrie Bradshaw for years already.
It was obvious. And my denial about it was more cringe than anything I was wearing.
My current frustrations stem less from a lack of understanding or feelings of being different, but moreso from the implication that what I’m doing is inherently disingenuous. It’s an implication that carries a callous disregard for my personal struggle: the extreme isolation, the overwhelming feeling of being “less than,” the anger at your maker for making you broken, and the medley of other misconceptions that took decades to unravel and parse.
But that’s neither here nor there. You either figure your shit out and recognize that every weakness has a strength, or you don’t and fall victim to your own demons.
Either way, it’s a luxury to have that choice.
Perhaps what stands out the most is that I’ve largely stopped thinking about this shit. Wearing women’s clothes isn’t something that requires active thought for me on a daily basis, beyond what colors I want to wear or what’s stuck in the dirty clothes pile.
The wardrobe is all women’s clothes.
There’s no debate when I wake up in the morning. I don’t wake up and contemplate whether today is “girl clothes” or “boy clothes.” I’m not into that ‘gender fluid’ shit. I’m a guy. I like girly things. So I have mostly girly things. It’s really that fucking simple.
Beyond that, I’ve gotten on with life. There’s so much more out there than sexuality and gender identity. It’s just one piece of the puzzle in the grand equation of our oddly emotional existence. Something that all humans must face at one point or another, but still just another stop on the journey to personal happiness.
If you survive long enough, there’s no way to avoid figuring out who you are.
Wearing a dress at my own wedding is something I’ve had on my mind for the better part of a decade, so much so that I forgot how concerned relatives would be about the spectacle of a man in a dress getting married to a woman.
If we were a gay couple or a lesbian couple, few would bat an eye. I think if I were transgender and fully transitioning, it would almost be easier for people to understand, even if they disagree with it politically or philosophically. Something about being a dude that likes to wear dresses just doesn’t compute the same way.
Less than a week into the engagement, my attire has been the biggest question by far.
I find myself forced to relive the same old stuff I thought we figured out years ago.
And perhaps strangest of all is reflecting back on the initial reactions when I first came out years ago. Most were banal and blindly supportive. In retrospect, they were suspiciously politically safe and lacking in depth.
The one note that stood apart was from my recently departed grandfather who, impressively, shared some very empathetic thoughts at 88 years old.
While his perspective was rooted in a different time, molded by the aftermath of the Great Depression, he was wise to recognize that “simple and straightforward” was largely an illusion maintained by repression.
“Accordingly, while I respect your right to be whom you want to be and certainly admire your courage and forthrightness... in the final analysis, I can’t relate to the concept on a personal level.”
There’s something particularly powerful about someone recognizing that they truly don’t “get it” on a personal level, but holding within the same thought that getting it isn’t a pre-requisite to respecting it.
Maybe that’s the difference between genuine support and blind support.
“I am still working on ‘a dude with a dress’ but I think I will probably get there.”
That might just be the most honest line I’ve ever read.
And, of course, he was wise to reinforce that there is no equality of understanding. Something that many people refuse to acknowledge.
And I suspect the root cause of much unhappiness.
This was excellently written and felt really relatable. Have you ever (internally) leaned into being visually distinct? I feel like I lean into the stares and think about it like "I'm broadening people's perspectives" or "I'm making it easier for others to express themselves."
Your great-grandpa's email was heartwarming, what a nice message. I agree with your point too. People understand the "what" in a narrow context, but often don't understand the "why." So when the "why" results in new "what"s, they are shocked all over again. The best I hope for is to make sure those close to me understand the (ever evolving) "why."