The Boyish Adulthood Of Gay Men

A recent conversation that I keep having with myself and Bobby is how should my style evolve—or should it?

I am an exclusive shorts wearer and very much embrace bright, ridiculous clothing. It’s less a means by which to seem young and wild but more of an expression of self and, in some ways, a political act associated with gender subversion in that it has been a fucking fight in some worlds to be able to wear shorts and bare my male legs just the same as women can bare their legs with skirts. It’s very much a part of my identity.

But I understand this has a limit. As you age and get saggy and wrinkly and transition to a different you, what worked in your twenties might not work for your thirties or forties or fifties or beyond. While I have it in my mind that I have to evolve toward a Nick Wooster style of mature adult male shorting, I’m still very much in the teen boy realm of male shorting. When do I make that switch though? When do my shorts have to go from boi toy mid-thigh to Japanese countryside mid-calve? When does the shorting have to go to pants? Or does it? This is a frequent conversation I have with myself.

This isn’t unique either: it’s a apparently a common subject for the aging gay boy. There’s a lot of identity politics in being gay outside of style like evolving from twink to bear or whatever other category you want or don’t want to assume. The fact is some looks are tied to age and you have to be aware so you don’t look like the old person trying too hard.

Enter New York‘s Editor At Large Carl Swanson who tackled this subject in a wonderful (albeit too long) essay on the gay male fashion midlife crisis.

I was thinking about this last weekend in the Fire Island Pines, the gay beach community I frequent now that summer’s here and whose core values are those of a day-drunk and barely dressed never–never land. It’s a place where everyone calls each other “boys” no matter how old they are.

I was worrying that I shouldn’t have worn my new swimsuit, which I bought online during a moment of procrastination, or fantasy, months back, when summer seemed impossibly far away. I think I found out about the brand on the never–never land of Instagram. My boyfriend described it, judiciously, as “fun” when I tried it on seeking reassurance, but I’m not so sure. (Despite my misgivings, I’ll still wear it all summer long, so long as it fits me.)

In the Pines, nobody is ever wearing very much, regardless of whether that is a particularly good idea. And to tell the truth, I’m often not either, and I was hoping that was okay. On a recent Saturday morning I was sitting on a pool deck among other men in their 30s and early 40s in similar states of abbreviated dress (one, truth be told, was just in a pair of briefs).

I know this feeling, particularly living in a warmer climate. To that effect, when you live in a city or an environment where dressing certain ways are a part of culture, you give yourself leeway. But does that ever end?


One of my friends, who is a lawyer, said he was worried about his brightly patterned J.Crew shorts. Were they too young? Another fretted over his very tight pants: This could be the last summer for them. Where is the line? How do you avoid looking foolish or desperate? Is dandy the opposite of sexy? Is it too tight, or too bright, or what if you just missed some other subtle cue that makes wearing something ridiculous?

While Swanson doesn’t quite land on anything definitive (The story instead wavers on style tips that are only applicable to That One NYC Gay.), it is an echoing of this admittedly premature conversation I’ve been having: when is it too much? Is it ever?

The reason why we (gay men) have this conversation is that we (like women and other objectified groups) are known for our looks—and we have to keep up with those Kardashians in our own way. The difference, and what Swanson only glosses over as commercialism, is personal taste, personal expression, and personal creativity through clothing. If you think you look good and that clothing is you, do you. Age doesn’t matter. Embrace your ridiculousness and fly that middle finger to anyone who really wants to step to you.

As my window stalls to close in terms of shorts, that’s something I’m embracing: instead of sticking to a style (mid-thigh shorts), think of it as a font. There are soooooo many fonts to choose from and you should try whichever best suits you at your time in life. Try something festive or bold or bright or understated or country or urban or heavy or light—or whatever. Try things out. Like that one phase in your life where you only used Helvetica and switched to Georgie, the moment you stop trying different fonts is probably the moment you surrender to the trappings of society instead of sticking to yourself—and that’s basically returning to the computer preset of Times New Roman. Who wants to do that?

That is the challenge of the boyish adulthoods of gay men: keep that boy alive by always listening. To shut him out is to shut out yourself.

Photo via.

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