Illustration by Carly Jean Andrews

How to Be a Guy: What I Learned My First Year Living as a Guy (at Age 34)

From the pain of being misgendered to the newfound pleasures of shopping at Topman

Okay, look: I’m tired. My personal life is a trash fire, my country just elected an actual fascist, I’m struggling harder than usual with dysphoria, I’m behind on every deadline, and I still have to figure out how the hell to get an Indiana birth certificate changed from out of state.

But you know what? Fuck it. I’m going to table world affairs and existential terror and all that fun, and do a year-end roundup. As of November, I’ve been living as a guy for a year, and damn it, I’m going to wax solipsistic about what I’ve learned.

And so, without further ado, I present: What I learned my first year living as a guy at age 34.

My gender is a much bigger part of how other people see me than of how I see myself.

My gender has always felt like an afterthought. Ask me to describe myself, and by the time I think to mention pronouns, you’ll already know that I’m an editor and writer, an enthusiastic but lousy cellist, a die-hard socialist, mildly autistic, queer and really into comics.

To me, coming out as trans felt less like a massive revelation than minor reification.

To the rest of the world? Not so much. One friend talked about feeling betrayed that I hadn’t shared such a fundamental detail of myself. People I’d known for most of my life complained that they felt like they didn’t know me anymore. It was like discovering that the people I thought were closest to me had seen me only in funhouse mirrors.

Maybe that’s why misgendering has finally started to get to me.

It didn’t, at first; at least not when it came from people I didn’t know. But these days, every ma’am is a kick in the teeth, a reminder that strangers’ assumptions mediate my social experiences a hell of a lot more than my actual identity.

Or maybe the problem is the cost. I spent most of my adult life as a queer, feminist woman in a male-dominated field, and most of my oldest and strongest support systems were communities of women. I’ve lost those to transition — without gaining any of the privilege they were formed to counterbalance, because people still read me as female.

Maybe it’s the fallacious assumption of a reward at the end of the climb: that the world owes me recognition for the hoops I’ve jumped through.

Either way, it sucks.

Living in a liberal city is a mixed blessing.

On one hand: I’m way less likely to be assaulted or discriminated against for being a female-assigned person who dresses and acts masculine. On the other hand: Living in a city where there are a lot of women who dress and act a lot like me leaves me with pretty much no way to code myself as male.

I really want to be on T.

I hedged pretty hard on the subject of hormones when I first started thinking about transition. The idea of starting on testosterone felt like a huge and largely one-way plunge — physically and socially. Most of all, I was terrified of how they might affect my relationships: how partners who had struggled with the idea of me with a more masculine identity would react when that identity began to take physical form.

For a long time, it was easy to defer that decision. My insurance doesn’t cover any transition-related expenses, so choosing how and to what extent to pursue medical transition was — and remains — a process of triage. Top surgery, which I got in January, felt more urgent; but it was also a safer option in some ways: a finite, self-contained process that did a lot to mitigate my personal dysphoria but had very little impact on my external presentation.

But the further I get in transition, the more certain I find myself that I want to take that route. The idea that more of my physical life and experience could feel as right and real as my chest does now doesn’t erase my lingering fears. But it does emphasize how off everything else still feels now, and what a difference every step has so far made. Uncertainty has become exciting: I want to discover what it means to be myself in as many ways as I can.

There’s a difference between change and loss.

I was really, really nervous about transition. I assumed at first that I’d settle somewhere relatively androgynous along the gender spectrum, and agonized about ways to preserve as many aspects of my female identity as I could. Letting go of them felt like betraying the sisterhood, like denying a crucial part of my journey to where I am.

At some point, I realized that I was hoarding those things like keepsakes: my birth name, the skirts I hadn’t worn in years but couldn’t bring myself to throw away. And with that realization came another one: that growing into my identity doesn’t erase my history. Those aspects of my life, of my experience, of me, are indelible. Taking my grandfather’s name doesn’t cancel out my grandmother’s influence. Giving those skirts to friends who will actually wear them doesn’t erase the times I danced in them. And if I feel obliged to spend my life looking back, I’m never going to have anything to look forward to.

Some things are easier than they look.

Last month, I stopped counting the number of times I’d used men’s bathrooms. I’m still cautious; I still use the women’s room most of the time if there’s more than one stall. But after that first, terrified try, it’s felt like an option in ways it didn’t before.

It’s also a good reminder that I tend to overthink things, to tangle myself up in theory when what I really need is to figure situations out through practice — or, for instance, to stop waxing philosophical on a “what I’ve learned” list and dive into the pragmatic details.

I’m suddenly pocket-size, and it’s weird.

As a woman, I was a smidgen over average height, with a vaguely athletic build. As a guy? I’m tiny. And there’s nowhere that stands out more than when I’m shopping for clothes.

At 5’7” I’m only three inches shorter than the average American man, but when it comes to clothes shopping I might as well be a Lilliputian. I should note that this is not a trans-guy-specific problem: My cis male friends confirm that it’s a huge pain in the ass for them, too. But there are a few perks to being a little dude: I can shop in boys’ departments, which cost less and significantly increase my chances of finding dinosaur-print garments in my size.

Topman is a trans-guy cliché for a reason.

For a long time, I avoided Topman, the menswear arm of British apparel giant Topshop, because literally every trans dude and masculine-of-center female-assigned human on the internet is obsessed with it, and I’m knee-jerk suspicious of anything that trendy.

Then, a friend sent me a gift card, and I found out why Topman is such a capital-T Thing.

Small dudes, listen up: Topman is one of the best-kept secrets of the fashion world. I’m 5'7" with narrow shoulders and a narrow waist, and Topman carries adult men’s blazers that fit me like they’re tailored, even with my narrow shoulders and waist. Hell, I don’t even wear their smallest size! Topman is also comparatively affordable — important when your body is changing and likely to continue to change; and/or you’re scrambling to assemble a wardrobe that supports rather than undermining your brand-new gender presentation — they’re great about returns, and they offer free tailoring in their stores.

Also, they seem to be committed to bringing back ‘60s plaid suits, and I respect that deeply.

That said, athletic shoes are fucking impossible.

Look: There is nothing wrong with pearlescent baby-pink and fuchsia sneakers with a lacy mesh overlay, and there is nothing wrong with dudes wearing pearlescent baby-pink and fuchsia sneakers with a lacy mesh overlay. That said, it would be really fucking nice if those weren’t the only decent running shoes I could find in my size. Again, I’m not tiny — but my feet are narrow enough to size me out of most men’s athletic lines, and right now, apparently that limits my options to pink-based palettes that run the gamut from “Florida resort” to “Hello Kitty.”

I think I’m actually pretty okay at this whole guy thing.

Yeah, I get read as female most of the time; but that’s probably not going to change until I’m on T; and ultimately, I’m secure enough in who I am not to compromise it in service to how other people see me. I still knit on the bus. I still get really excited about comics that focus on intense teen-girl friendships. I’m still me, and being a guy is a fundamental part of that package, however I choose to perform it.

Baseball caps, though.

I’m not a sports guy, but my Chicago roots run deep, and this summer, I traded in my beloved cabbie hats for a Cubs cap.

And suddenly, people started calling me sir.

At first, I figured it had to be the sports thing, but then I went out in a plain baseball cap and got the same response. Apparently baseball caps are magical gender camouflage. Who knew?