Why My Hat Says “BOY” on It

The author in a “BOY” hat.

Photo courtesy of Christin Scarlett Milloy

You may have seen these hats around: baseball caps, most commonly black, with “BOY” printed or embroidered on the front panel. I’ve seen a version that also has “GIRL” printed on the underside of the visor. On the websites that sell them, the hats are most commonly seen on men. Interestingly, though, in the real world, you will chiefly find them perched atop the craniums of women, including (or, I think, especially) queer women.

How awesome is it that our society’s progression in the handling of gender identity and expression, and the new freedoms to experiment therewith, have evolved to the point that people are actually beginning to play around with the very labels of gender identity … as a fashion statement?

Why would a woman wear a “BOY” hat? I can think of three reasons. 1) Simple irony. I’m not a boy, but my hat says BOY. Ha! 2) Women who are queer and want to make a statement. (I dig it.) And 3) Women who have reason to think of themselves as being, in some way, boyish. But what is “boyish” in this context?

Strength, intelligence, and sporty traits are said to be boyish. Preening, grooming, nurturing, and caring behaviors are said to be girlish. As a society we pretend that these ideas are the vestige of a bygone era, but damn do those notions ever have a nasty way of persisting in our popular consciousness. And media. And clothes. And toys. And so on.

We know these gendered associations are often false. We know females can and do play sports, and males can be gentle, caring fathers and sensual, considerate—even submissive—lovers. And while I optimistically perceive a general trend toward acceptance, unfortunately these “gender-inappropriate” behaviors are still unfairly policed and punished in society.

When a woman chooses to express herself with a big bold label like “BOY,” something that conventional wisdom holds she most certainly is not, it provokes people into thought: She’s identifying herself, plainly and publicly, with traits that are not (but could and should be) associated with her gender, and she’s calling out the bullshit gendered association of those traits at the same time.

Back when I was a boy, in the standard culturally accepted way, before I understood my trans identity, I used to express myself by adopting a more feminine male expression as much as possible. I wanted to distance myself from my masculine peers, and I did this in a number of ways. While maintaining an ostensibly “male” presentation, I wore makeup and effeminate jewelry. As a teen and in my early 20s, I would often wear women’s tops and jeans as part of my “male” wardrobe (because they “fit better” and accentuated my “boyish curves”).

There was a space in gay male culture, at that time, for extremely feminine guys, which, I feel, has somewhat disappeared. Conjecturally, I suppose it may be because a lot of the “guys” who would be carving out and inhabiting that space are, these days, identifying trans-feminine and transitioning to female (or non-binary) identities much earlier in life.

Immediately upon transitioning to a female identity, acceptance became paramount to me, and I cared far too much about passing—that is, for people to read and accept me as a woman, without being able to tell I was trans.

I thought that acceptance and passing were synonymous. As such, I kicked my affectation of traditionally feminine expression into overdrive: wearing makeup, donning conservative professional women’s attire to work, heeled or wedged shoes, et cetera, ad nauseum.

The thing is, makeup was a nuisance and never felt right. It’s nice to “doll up” occasionally, but goodness gracious, on a daily basis? I hated it—I figured maybe it was because I hadn’t had a mom or sister teaching me the ropes from an early age: I had to crash-course in my 20s. Overtly feminine clothing, clothing that exposes or objectifies my body, makes me uncomfortable. Again, I blamed my lack of experience at conventional hetero-femininity for my lack of confidence in myself as a woman.

It never occurred to me until much later that what I had were not specifically trans problems, but problems common to all women. The pressures to express and behave according to an unfair and outdated standard of gender roles or face social consequences? That’s a problem older than trans.

I play retro video games. I watch Star Trek obsessively, code websites for a living, and argue about Battlestar Galactica with my friends. Sure, I date and go to clubs, I even dance occasionally. But my idea of a good time is actually Dungeons and Dragons, or going to a board game café, or cuddling at home (Deep Space Nine works wonders for this). What kind of woman am I? I’m a geek.

Some of my co-workers who, like me, work on the technical side of things and don’t have to interact directly with clients, choose plainer more comfortable clothing, with flat shoes or sneakers, like I prefer to wear. (By the way, it’s hard to find women’s shoes in Size 12.) I’ve seen those same women at fancy company events like the Christmas party, so I know I’m not the only one who thinks that makeup is for special occasions. I’ve come to let myself believe this means I’m not alone, and I like to think my general disdain for certain trappings of femininity is not because I’m trans.

But really, I worry. I’ve internalized some of society’s criticism, because it’s impossible not to, when so many people hate and belittle you for what you are. Boyish. Am I like this because that’s just the type of woman I am? Or was it because I was brought up as a boy? Unfortunately, the fates have conspired such that I will never definitively know the answer, and sometimes that eats me up inside. But there comes a point when you’ve simply run out of fraks to give: I have to be true to myself, and live the life I lead, as I am on any given day. And today? I’m a little boyish.

So, I ordered myself a BOY hat, aqua-colored with purple embroidered lettering and a purple visor. It matches great with my wardrobe (because coordination is important, regardless of how your clothes are gendered). It’s comfy to wear, it looks great on me, and it reminds me of a time when life was a lot of fun. The lesbians in my life think it’s awesome, and it has already prompted some really fun conversations with straight cis people where I had the opportunity to educate them that their “clever” comments and pointed questions were examples of gender-policing, transmisogyny, and micro-aggressions. I love this hat.

Being a woman isn’t about nurturing, or submitting to men, or painting colors on your face. Anyone can do those things if they want to, but the world stamps that role on us automatically. But binary gender roles are coming to an end: A woman can be anything she wants to be. Including, occasionally, a boy.