Drowning In Wool: Gay Masculinity and Me

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About Zach Stafford

Zach Stafford is a Tennessee writer living in Chicago. He can be found writing for various media outlets, both on-and-offline. While not writing he works in research and HIV Prevention. Feel free to tweet him at @ZachStafford.


  1. A wonderful read, and a lot to think about. Thank you.

    (I get harassed sometimes for being a lesbian who dresses/acts ‘too straight’.)

  2. In many ways I was neurotic with this ritual, but it was something that brought me a sense of control in my life. At thirteen, control is something one desires as their body changes, they start high school, and if you are like me: you realize you’re gay in a place where that’s the last thing anyone wants to be.

    I was seen as “very gay” since elementary, but only told so (directly) in high school. I didn’t know what “gay” meant until I was 16-17, and it was very abstract (I didn’t think of myself as gay ever, and didn’t know a gay person).

    I’m a trans woman, and transitioned at 24. I’m androgynous in body, I wear androgynous clothing (but it’s probably considered too feminine for gay men because of the hard line drawn at skirts, not because of how fashionable it is).

    I never really obsessed over the clothing I wore, even way less when my only options were bland, bland and more bland. Men’s clothing is drab (boring) and “all-the-same”, as if even having the option of picking something was a bother. Only very expensive suits and such even have many options, the rest is all the exact same as your left and right neighbor, and all other men in the room. White or black socks, maybe grey or blue, good luck finding something else. No capris for you. No legging for you. Most clothing is not stretch, and it’s certainly not embroidered. As if the male body was considered ugly and meant to not be shown. And it’s clothing ugly on top so men don’t draw attention.

    Because we still live in a world where men are not celebrated for being effeminate, but instead ridiculed and sometimes face different forms of violence.

    The word effeminate itself is an insult, it implies that men can’t be feminine, only some inferior-type of feminity that’s considered an inherent insult. I prefer to use feminine than effeminate, for the same reason I use masculine and not “ugly” for a masculine woman.

    Her remarks would be sweet vignettes like: “Oh that is cute, I don’t see a lot of the other guys wearing that.” Or her personal favorite, “You dress really nice for a guy!”

    That’s rather condescending, as if guys were inherently slobs, but you’re the exception. How about telling her “You’re really intelligent for a girl”, it’s about as offensive.

    What high school student is out there right now sitting on his bedroom floor obsessing over his clothes to make sure he looks just right so he doesn’t have to deal with as much teasing?

    I dressed as dressed-down as possible. A no-logo loose black t-shirt and loose pants. Very unconspicuous, even hiding my small size (which was also a source of teasing). I STILL got teased. And in elementary, beaten. I was too curious, saying inappropriate things, not witty enough, too aspie, too small physically, too alone (no friends) so an easy target – and the one thing that got me called gay: my body language got read as obviously female (and I didn’t know about that one until I was 23). No clothing would have made it better. Dressing fashionably would have only attracted MORE attention.

    Plus I don’t really care for popular fashion. I like good-looking clothing, but I make my own fashion. My clothing lasts me decades if its good quality, and it still looks good. Because it doesn’t depend on “being in”.

    • Ah yes, I mostly wasn’t sexually attracted to anyone, almost entirely asexual.

      I later learned I was a demisexual pansexual person, but only post-transition (25+, I’m 30 now) as I only did kissing before that, and was deathly afraid of the mere idea of it progressing to sex (at 16, as I wasn’t comfortable having sex with what I had), although I dated that girl for a little while. Since she was expecting me to be leading and dominant, and I wasn’t, it was all easy to stall things until she got bored and tried hitting on my brother.

      As a bonus I learned to kiss well at 12, and had extra practice at 16 (girls both times). I got sex the first time at ~25 (giving oral, on a guy).

      My sexual orientation didn’t really matter, and I didn’t “develop crushes” based on physicality. That’s no doubt why I never thought about it until transition. I didn’t find “virginity until 25″ to be anxiety-driving (I can easily go without any sex, including manual, for years), though people took it as an extra sign I was gay, of course.

  3. David May says:

    This tale is all too familiar. Back in the 1970s I was doing pretty much the same thing, but balancing the blousoned-shirt-and-bell-bottom-jeans pseudo-hippie look popular at the time. One could only push the look so far before being called queer: Nothing too gauzy, nothing too matchy, and never looking like I put too much effort into my clothes. Eventually I succumbed to T-shirts and jeans most days, if only to make like easier, saving the pseudo-hippie attire for weekends and parties.

    This is a path a lot of gay men must follow. Eventually we land on the wardrobe that fits our own understanding of who we are as men and our place in the world. Certainly straight men must experience something akin to this: certainly in Italy most men are as obsessed with clothes and grooming as women are, so perhaps this phenomenon is more universal than we thought.. One wonders. Guys?

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