Digital Letter: To those who might wonder why I, a man, wear women's pants

Because women's pants fit my body. You shouldn't fit into clothes—clothes should fit you.

Dear those who wonder why I, a man, wear women’s pants,

I remember when I first decided to try on women’s pants. It was in a thrift store in Brooklyn. A Goodwill, I believe, near the Barclays Center. Even in a place with liberal tendencies and a comparative openness like New York, I still felt a fear wandering into the women’s section. A block froze in my chest.

I ran through excuses in my head for why I might be in that aisle, in case other shoppers looked at me strange or if someone asked why I was there. “Oh, I am shopping for my girlfriend,” “Oh, I have a friend that asked me to pick something out for them,” “There’s a costume party tonight.” All lies. I wanted pants for everyday use.

I crossed the border. There was simply just more. More clothes, more cuts, colors, shapes, sizes. More. I didn’t wish to be a woman, I just wanted pants I liked and that fit. I ran into a familiar frustration when searching for clothes designed—through the centuries—for my own gender, my own quadrant, the socially constructed area for me, a dude, a man, a “performer” of masculinity. I found nothing in the men’s clothing. Just beige and black pants, jeans, all too big or too long for me. Brands uninspired, clothes processed out of the long line of conformity.

Being born with scoliosis and clubbed feet, I needed ten surgeries in my youth, which left me short. I am 5’2’’. That may or may not be rounding up my height. My spine is curved and bolted with titanium rods, including two-inch screws that penetrate parts of vertebrae and pelvis. Below my knees, my legs are broom sticks, just one-measuring-cup of muscle for my calves, and solid ankles that don’t bend. Tiny feet, under 7s in men’s shoes. Having this body has left me with a lifelong challenge of finding clothes—pants and shoes in particular—that fit me.

The fear, while in the aisle built for women, clacking the hangers on the silver poles, back and forth was real. I felt I had betrayed a long history of trying to wear the “right” thing. I feared what others would think of me.

I first felt aware of this fear in middle school; the source for when many become aware of gender limits. Or, as an old professor of communications once told me, “They tell us in elementary school, telling you which bathroom to use. No, they tell you with the blue or pink blanket when you’re born. Right from birth it starts.”

So, yes, my awareness of gender was instilled at an earlier age, but a touchstone in my memory came when I wore my sister’s jeans to school on accident as an eighth grader. This was 2003 in the south end of a southern Colorado town. Very south of Brooklyn in sensibility and culture.

I was late and needed to walk to school. I couldn’t find clean pants. I pulled some jeans out of the dryer, thinking they were my own. They draggled on the ground—just as my own pair had, as baggy was in, and no store-bought pair fit my shorter legs anyways—they all drug a little bit for me in these years. This was a low-cut boot pair, flared at the bottom with a bit of sparkle on it—I didn’t notice the sparkle until I was in the belly of the school. I barely survived the day.

A science class, in particular, was difficult to endure Verbal hammers from the boys. An outrage of wearing something outside the lane of what boys were supposed to wear. The bullying was non-stop vitriol: gay, the main insult and bit of shrapnel at every verbal toss, was the word in high use. In the days of the early aughts, gay was short hand for something bad, terrible (I’m not pretending that it isn’t still nowadays, but I imagine it has lightened somewhat, at least in some corners of the US. I mean, I saw the word proudly on a dishtowel in a Target in Alabama, up for sale. So things have changed a bit).

I’ll let you fill in the other words—the thorny offenses that spring from that fear of difference, gayness, the blades of homophobia. I was so terribly gay for wearing these pants—these girl pants. I felt wrong and terrible, and rushed home after school, and threw them off. I meant to never speak of it again.

I wasn’t gay—as if that mattered. It didn’t matter what my sexual orientation was, especially when it came to wearing pants. But the world I grew up in, came of age in, required men and boys to look a certain way, and women another. There were baselines, standards. And pants, the pants you wore based off your gender, was one of those standards. If you broke those standards, it was a violation, a failure, a jolt of unwanted queerness.

I grew out of that world, far and beyond, by the time I had a job in New York City and was shopping at the Goodwill in Brooklyn. But the residues, the limits of what I could wear, were still carried within me. I felt like I was doing something wrong in the women’s section, looking for pants. It felt weird. I also feared being seen by some manifestation of those middle school boys morphed into adults. They followed me in my head.

Strangely, though, fighting that feeling that I was doing something taboo and wrong, I also found another feeling: a release of joy. For I found something I rarely found in the men’s section: pants that fit me.

Pants that would not need to be hemmed. Pants that fit tightly across my legs, around my ankle, that hunkered over my oddly, shaped by scoliosis limp and walk, shaped hips. They fit!

In addition, I found something else I craved from my clothing, but did not realize I wanted: color. I found Smurf blue, tie-dye green, floral patters, mauve, Wisconsin-cheddar yellow. If clothes are supposed to reflect who you are, and match your identity, these pants I found in women’s section—many in thrift stores—had done just that.

In these pants, I started to feel something else I hadn’t felt in clothing: being seen. I loved the compliments I got in public. I liked being noticed and being complimented for my appearance. “Nice pants” became something strangers or friends at a party would start to say about me. It felt like a karate chop to the old days of middle school, high school and early college; it felt like a Star Wars force crush of the self-hatred that grew within me. I hated myself because I never thought I was beautiful or good looking, and by extension the clothes I wore never uplifted or changed this feeling. Not any longer. Women’s pants had started to change my definition of what clothes could do for me. Finding pants that actually fit my body and personality made me feel good—sexy, even.

If clothing is a second skin, a transmitter of your identity, then it should be true that you don’t need to fit the clothes, they have to fit you. You have to remake the clothing, or rearrange from the departments forbidden to your body, to match your desires, needs, and wants. It’s a hack, a hacking of the rules and tools to reach your purposes. To buy clothes not “made” for you and to wear them, is a way of hacking a system, stirring up conformity.

This is also to say, I have extreme privilege to pick my clothes. I have resources and stores and abilities to pick clothing I like and want. Clothes should be made more sustainable and more accessible to more people. Why can’t women’s pants, for example, have bigger pockets? Some barely have enough room for a pistachio nut. Or as my wife points out, toddlers have bigger pockets than many women’s pants. What does a toddler need that a full grow person wearing pants doesn’t? Furthermore, people with disabilities, people who have larger bodies, all should have more options when it comes to clothing. If clothing is part of identity, everyone should have the ability to add to their identity however they choose. More sizes and cuts and options for all.

For the record, I wear men’s pants, too, when I find a pair that fits.

But that’s just it, isn’t it—labels are helpful for categorizing, finding items, but they shouldn’t be roadblocks or walls? People should be allowed to cross boundaries. Cross into new aisles because there might be something there they might find to their liking.

We should be allowed to wander. The gaggle of hate in someone’s head should be quieted. Not be a promoter of fast fashion, or materialistic needs to create identity, but clothes matter. Clothes, among many other things, can be reimagined, and be a form of self-love, and self-discovery. Then, maybe, a map will be redrawn, a mind will open.

ENDIT.

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Blurbs & Shoutouts

• Here’s the NY Times article that inspired this letter. Shane O’ Neill, love his coverage, but especially here telling readers why unbuttoned and unzipped is in style.

• Speaking of media makers, Max Chafkin has become one of my new favorite journalists and nonfiction writers. He’s a features editor and tech reporter for Bloomberg where he takes deep dives on anything from Twitter, the AirPods empire, to Zuckerberg’s struggles to conjure the pearly metaverse. There’s also, his book The Contrarian—a biography of the venture capitalist and influential investor Peter Theil. Silicon Valley can feel like a myth, a Mount Olympia caked in neon and microchip metal. This book though, along with the need-to-explore story of Theil, tells us the story of how the valley rose to a hot, broiling fireball of power.

• Hey check out this fascinating film from my colleague, Chris Gauthier at MoS who, before he got his job at WaitWhat, worked on: Mud Frontier: Architecture at the Borderlands. Here’s the description from the website: a feature-length documentary about Studio Rael San Fratello’s work to connect contemporary technology with the legacy of pottery making and adobe architecture in the Southwest United States. 3D printers are used to make adobe bricks. Check it out!

• Also check out Transgendermap.com for info on the importance of clothing for transgender people, and a good general resource for information on transgender challenges, triumphs, and other good stuff.

• Take a listen this week to Masters of Scale—and see our new website! Reid Hoffman talked to Noom’s Saejue Jeong, and Masters of Scale’s Rapid Response, hosted by Bob Safian, spoke with Shake Shack’s founder and restauranteur, Danny Meyer. Of course see Meditative Story and Spark & Fire from WaitWhat. Hey, we are hiring! If interested, check our jobs.

Peace and Love—Tucker