How Learning to Dress Myself Helped Me Understand My Trans Identity

There’s a part of me that is overwhelmed by the possibilities, by the fact that I finally look the way I used to only imagine I might.

My students joke that I dress like a cartoon character. I have a uniform, like Arnold with his flannel and sweater, his blue cap. Although the actual clothing varies a bit—a different graphic tee, gingham rather than plaid, a different color—they’re not wrong.

In the summer, I get too hot to wear anything but shorts and a T-shirt. But for the rest of the year, my daily uniform is a pair of jeans and work boots, a T-shirt, and an unbuttoned Oxford with the sleeves rolled up (I own ten versions of the exact same shirt in various colors and patterns).

Despite my uniform’s simplicity, it’s difficult to put together. I’m fat and it’s not always easy to fit into clothes I actually like. To buy pants, I have two options: Go to Walmart and buy dad jeans, or order them online. Stores don’t typically carry anything bigger than a thirty-eight-inch waist and I wear a forty-two or forty-four, depending on the cut. I buy XXL shirts to ensure the buttons all comfortably fasten. This means the sleeves are always too long and the shoulder seam is about a half-inch too low.

There simply aren’t many options for a guy with my body shape. When I find something that fits—American Eagle Slim Core Flex jeans, SONOMA Goods for LifeTM Oxfords from Kohl’s, Target’s Goodfellows crew-neck T-shirts—I buy it in every color. It makes things easier.

This is why I accessorize: I am a sucker for a good tie; I have a shark tie bar and football cufflinks; I am picky about my glasses. These are things I can pull off at any size.

But it’s also because I don’t know how to dress like a man. For the first twenty-three years of my life, I spent my days trying to fit in as the woman everyone thought I was.

*

In high school, at the mall with my mom, she would push me toward more feminine clothes. She’d take me into Lane Bryant and convince me to try something other than my usual gender-neutral jeans and T-shirts. I’d always leave with a couple of outfits I hated, clothes that made me feel like I should be heading to my job in human resources instead of attending the tenth grade. I’d wear them a couple of times and then “lose” them at the bottom of my laundry basket.

Later, once I had a job and could drive the fifty miles to the mall with my friends, I’d try to buy my own clothes. I’d watch as they sifted through clearance racks at Charlotte Russe, American Eagle, and Aeropostale. I’d pretend to do the same. But even if I found something in my size, I doubt now that I would have bought it. On the rare occasions that I did find something that fit, I usually hated it.

At the time, I didn’t have the language to describe why I hated these clothes. I told myself that it was because the clothes were uncomfortable—and they were. That it was because the clothes didn’t fit me right, which was also true. But I told myself I wanted those clothes.

Everything would change, I thought, if the right stores just made the right clothes in the right sizes, or if I just lost weight. It never occurred to me that my discomfort in those clothes might be more complicated, might come from someplace else.

It never occurred to me that my discomfort in those clothes might be more complicated, might come from someplace else.

On one of these trips to the mall, I found myself looking longingly at the men’s department for the first time. I realized that I’d been staring at the clothes and watching guys my age—some of them even the same size as me—shop for something other than T-shirts and head to the cashier with clothes that I wanted.

I wanted them, suddenly—those clothes. But I didn’t know what that meant, or what to do about it. So I returned to the women I came with, to pretending.

*

In college, I was away from home for the first time. I tried to fit in, to be the person I wasn’t in high school. I put on make-up. I let my hair grow out and permed it. I got contacts after years of glasses. I made it about a week before switching back, unable to put them in.

A month or so into the school year, I stopped trying to be someone else. The pictures of me from that year shift abruptly. I stopped wearing make-up. I would put on jeans and a T-shirt to go to class. I rarely bothered to do anything to my hair other than brush it, still wet from the shower. Eventually, I went to the hair place next to Wegmans and paid ten dollars to get all of my hair cut off. It almost—but not quite—looked like a boy’s haircut.

And then, the year I turned twenty-one, I started watching videos of trans men on YouTube.

In their early videos, they all looked like me and sounded like me. But then they began talking about the ways their bodies were changing from hormones—about feeling their voices become lower, about the hair that started to show along their jaw lines. I watched them religiously in my apartment at night, lying on my stomach in bed with my laptop, in awe as I watched video after video, witnessing the first eight months of someone’s transition in a matter of minutes.

That summer, not long after I started watching the videos, I was learning about transgender people in one of my classes. It started to click. I still hadn’t said it out loud—not even to myself. But I would start thinking about boys’ names that I liked: Alex and Andrew and Jack. I’d catch myself thinking, “Nah, I’m not a Jack,” before I could stop myself. I’d spend the next few days pretending everything was fine. Then I’d find myself, again, on YouTube.

One night, I couldn’t sleep. I’d been watching videos by this one guy; I think his name was Justin. He’d just had top surgery and was showing off his newly flat chest, his scars.

I got out of bed, found an old Ace bandage, and looked in the mirror as I wrapped it around myself, flattening my chest. It hurt, but I liked the way it looked. I put on a T-shirt and stared at myself in the mirror for a while, in awe of what my body could look like, how it made me feel.

Soon after, I went to Walmart in the middle of the night. Rather than looking for my usual gender-neutral options, I went to the men’s department. I found a pair of bootcut Wranglers in a reasonable size and the most masculine John Deere shirt I could find.

It was late, but there was still an attendant at the dressing room. She asked me how many items and I said, “Two.” She handed me a tag and unlocked a door on the men’s side, ushering me in.

I shut the door behind me. I looked at myself in the mirror and felt an odd sense of pride that she thought I was a man. Even though the jeans were far too small, even though it was a T-shirt I never would have worn, I tried them on, picturing myself years from that moment, in that same outfit. What would I look like with a little bit of facial hair? How would this T-shirt fall on my body once I didn’t need the Ace bandage?

I would start thinking about boys’ names that I liked: Alex and Andrew and Jack. I’d catch myself thinking, “Nah, I’m not a Jack,” before I could stop myself.

Clothes like this took over my wardrobe. I hadn’t spoken the words yet, hadn’t even written them down anywhere, but I thought about it almost constantly. The more I experimented with clothes, with the way I looked, the more it felt right.

I’d wrap my chest in an Ace bandage, put on men’s jeans and a plain black pocket tee, add a baseball hat. I’d look in the mirror and feel, for the first time, like I wasn’t pretending—even though I was, wasn’t I?

*

By my second year of graduate school, I wasn’t pretending anymore. I changed my name. I started getting biweekly injections of testosterone. They changed my voice, gave me some facial hair, changed the shape of my body. Suddenly, I needed smaller jeans; they fell right on my waist. I swapped my Ace bandage for an actual binder. I shaved my head.

One of the guys in my grad program was cleaning out his closet one weekend and gave me a bunch of his old Oxfords and polos. So my less casual wardrobe suddenly consisted mainly of Oxfords and polos. Still, when I wasn’t teaching, I stuck to my comfort zone of old jeans and T-shirts. My mom, after I came out, years before the Netflix reboot, looked at my closet and said, “They need to bring back Queer Eye for the Straight Guy so I can send you on it.”

When I had a job interview the year after I graduated, my thesis advisor told me—without me even needing to ask her—to go buy a suit.

I dreaded the prospect. I’d heard rumors of people asking, “Which way do you dress?” I wasn’t sure what to say, afraid that if I said the wrong thing, they’d know I was lying. Even in my liberal city, even with two years of testosterone giving me a beard and a receding hairline, it felt risky, almost dangerous.

But the guy who helped me was patient. He found a charcoal gray suit that he promised would fit with alterations. I held my breath as his hands took measurements, pinned things in place. I don’t think I exhaled until he stopped without comment, without noticing anything.

When I went back the next week to pick it up, he had a shirt and tie ready for me. He had me try them on—the new shirt, the perfectly altered suit. He taught me how to tie a double Windsor knot, instead of the “school boy” knot I’d learned from YouTube. I stood in the three-way mirror, on the pedestal a step up from the floor. I couldn’t breathe again.

Wearing that suit, I felt like a man for the first time.

I’d looked male for a while by then, but I looked younger than twenty-six, partially because the testosterone was still taking its time, partially because of how I dressed. Seeing myself in that mirror, it seemed like my shoulders were broader, my waist slimmer. Though the dress shoes didn’t give me any extra height, I felt taller.

I vowed, then and there, to dress like this forever.

Of course, I didn’t. What I didn’t realize then is that formal clothes aren’t actually that comfortable. I get hot easily, so I’m constantly taking off my jacket, rolling up my sleeves, fanning myself with the program at weddings. Dress shoes hurt, no matter how many different pairs I try. I wish I could just wear my worn-in work boots. And, without someone around to tell me, I have no idea how, exactly, to wear those clothes anyway.

A couple of years ago, after I started the job for which I bought the suit, I bought a new blazer from the clearance rack, thinking I’d step it up a bit. I wore it to work, matching it with a pair of light chinos and a dress shirt and tie. My students, who had just discovered that I wear my favorite red plaid shirt to campus at least twice a week, kept stopping me in the hallway to compliment me. I felt great.

Then, walking from the mailroom back to my office, I heard someone call my name. It was my friend Debbie, a literature professor and one of the best-dressed people on campus.

“You forgot to cut the vent open on your jacket,” she said, the same way you would give a friendly heads-up to someone whose tag is showing, or whose fly is down.

I recognized all of these words, but could not, for the life of me, figure out what they meant in this context. My face must have given me away.

“The vent in the back,” she explained. “They sew it shut so the jacket doesn’t crease in the store.”

She led me to the main office to borrow a pair of scissors. The department’s administrative staff, all women, laughed as Debbie showed me how to cut the thread. (Then she asked, “You know about the pockets, right?” Reader, I did not.)

And it’s not just that. Despite losing weight, I still struggle to find clothes that fit—jeans that are big enough to fit around my waist, but not so baggy that they collect around my ankles, around my thighs; shirts that are loose enough that the lines of my binder don’t show, but tight enough that I don’t look like I’m wearing someone else’s clothes.

Despite all of this—the struggle to find the right clothes for my body, the struggle to figure out what I should or shouldn’t be wearing, or how I should or shouldn’t be wearing it—I still love clothes.

I remember, sometimes, the feeling I used to get when I’d stand off to the side and look longingly at the men’s side of the store. The longing to wear those jeans or that T-shirt, to wear a shirt and tie for a special event instead of a dress, to just run a comb through my hair instead of standing in the bathroom for what felt like hours while my mom used the curling iron and blow dryer and hair spray.

When I go shopping now, I know that those clothes are all open to me. Maybe they won’t fit, maybe I won’t actually like them once I have them on, but no one is going to stop me from looking.

And I do look, all the time. I go to Kohl’s or TJ Maxx or Target at least once a week, looking through all of the new merchandise, taking a huge pile into the dressing room with me. I try on sport coats and dress shirts, polos and chinos. I look through the ties, trying to imagine what I might look like in that bowtie, or that pair of suspenders, or with those cufflinks.

There’s a part of me that is overwhelmed by the possibilities, by the fact that I finally look the way I used to only imagine I might.