My Midlife Style Crisis — and Yours

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Growing up gay means, eventually, coming to some understanding of what it means to be a grown-up gay. This can be harder than you think: the procession, the outside markers of adulthood, even approaching middle age, can pass by unnoticed — or at least easily be ignored — as people continue to describe you as “boyish” right through your 30s. It wasn’t so long ago that my 6-year-old nephew asked me if I was a “teenager” or a “daddy” because he couldn’t figure out how to categorize me among the suburban adults he usually interacts with. It must have been either my haircut (admittedly, at the time, somewhat gender-nonspecific) or my outfit (I think I was wearing a pair of orange-and-green shorts from Opening Ceremony, a shop within lunchtime meandering distance of my office that caters to, from what I can tell, pasty, resolutely with-it FIT students whose prosperous parents still pay their credit-card bills.)

I was clearly giving off mixed signals, not only to 6-year-olds, but also to myself. I’m not always sure just what my shopping parameters are — among other confused notions of self I suffer from — now that I’ve become the age of those FIT students’ professors. And it’s now been a long, long time since anybody carded me at a bar.

Like a lot of “creative” New Yorkers, my life hasn’t changed much since my postcollegiate years. I often feel like I live a kind of modified adulthood: no kids, no mortgage. My only big-boy responsibility is to my somewhat-pampered 12-year-old dog. At my age, my parents had three teenagers, three cars, and a four-bedroom home, whereas I can’t really afford a proper apartment — you know, with a real kitchen, maybe a dishwasher.

And so most of my life is suspended in a kind of self-indulgent parabohemia, and it’s led to a self-indulgent crisis of self: How do I dress given who I’ve become? Clothes, somewhat to my surprise considering how much contempt I once felt toward the fashion-y, have taken on a great deal more meaning to me — in the sense of helping me understand and communicate where I am in my life — than I ever expected.

Obviously, I’m not alone in this: Since New Yorkers don’t spend their days in cars, our outfits define us to each other and the world. A few years back, I went to the 40th-birthday party of a (straight) friend, an old roommate, who’d moved to Montclair with his family. I remember being struck by how all of the 40-something suburban dads were now dressed in the clothes they wore when they were young and still living in the city — ringer T-shirts and vaguely flared, definitely out of date jeans, dressing in a version of cool that harked back to when they were cool. And I realized then that there are two kinds of midlife apparel crises: still dressing like you did when you were young, and dressing like actual young people do today.

My problem is mostly the second, even as my hair thatches gray and that Opening Ceremony shopboy now calls me “sir.”

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). Meanwhile, on the balcony of the house behind us, visible through the scrubby trees, a for-some-reason-naked man was scampering on the furniture with a Mylar cape around his shoulders to the tune of Rihanna’s “Work.” So at least we weren’t him.

No, we were drinking coffee, and we were talking about what we won’t wear anymore, or won’t ever wear. 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?

Later, I bring up the topic with my beach-house mate, a 46-year-old architect — trim and, yes, still boyish — who spent the weekend in a short patterned suit instead of a Speedo. Despite the fact that he is wearing red sneakers, he mentions that he was thinking about giving up on his Jack Purcells, which he’s been wearing since high school. Why? “Too young for us,” he says. Meaning me, too. “There is a guy in my building, a photographer, who wears them, and I always think, God, why don’t you dress like an adult?

What else does he avoid? “Anything trendy.” What does that mean to him? “Like, five years ago, when everyone started wearing skinny jeans rolled up. I thought: Can’t wear that. Too young.” (In response, that indelible phrase from “The Love Song of J. Alfred Prufrock” popped into my head: “I grow old… I grow old…”)

I confess I did wear them rolled up, following that trend. (You know that anxiety: “I shall wear the bottoms of my trousers rolled. Shall I part my hair behind? Do I dare to eat a peach? I shall wear white flannel trousers and walk upon the beach.” I didn’t identify too strongly, I admit, when I read that poem in high school. Now I get it.) I’m a small guy, so most things don’t fit me without tailoring, but I’d still hem my jeans a bit too long, just to roll them up again. Lately, however, as fashion pants have gone shorter still (as high as mid-calf), I went and got a couple of them re-hemmed to my actual leg length.

Maybe you can blame some of this on Thom Browne, who shrunk the man-hem, but as my housemate points out, since he happens to work near their offices and sees the staff out in public fetching coffee: “Suits with short pants look fine on young people. But the older guys who work there and also have to wear those suits, well … ”

He shakes his head.

He includes in this latter group Thom Browne himself, whom he also spies on occasion, his well-toned calves on trademark display.

Between the relentless self-censorship (Can I still get away with this? Should I?) and the fierce judgment of others (he really shouldn’t wear that, so maybe I shouldn’t either), I’m frankly surprised I even get dressed at all.

These are some of the questions I don’t want to have to ask myself anymore:

How short do I wear my pants?

And how high do I wear my shorts?

This matchy thing, is it for me?

If drop-crotch pants need to be in my wardrobe.

Or those skirty shorts.

How scoopy should I wear my T-shirt?

And how droopy?

What about these?

Or these?

All that fashion is part of someone else’s journey, someone for whom 1990s references are as fresh as their complexion.

I moved to New York two decades ago from Virginia to both lose myself and try to find myself, and I’m sometimes a bit surprised at just what I’ve become. I’m never really bored, or I try not to be, which was as much as anything the goal. In the process I’ve run through many iterations of myself: preppy postcollegiate Carl, when I was trying to fit in at the New York Observer, with the wire rims and preppy blazer; grunge downtown Carl, with the sparse facial hair, thrift-store clothes, and best friend who wore a slip in public; tentatively fashionable Carl, when I got a glossy-magazine job (back when that was an upscaling career move) and dressed, as one friend put it, like an older person trying to look young; and then downtown bobo Carl, when someone turned me on to APC and my then-boyfriend’s then–best friend started a Marc Jacobs–ish menswear label called Loden Dager and I got all my snugly cut clothing at a discount. Almost ten years on, a few of their shirts and jackets remain important parts of my wardrobe, but that shrink-fit era — my ex used to joke that if you could lift your arm then you needed a smaller size — now seems less relevant to me. Best to avoid being that middle-aged gay man straining the shoulders of his too-small dress shirt, aching suit buttons poised to pop.

For reasons unrelated to undersizing issues, Loden Dager itself went out of business, and the designer, Paul Marlow, now makes bespoke suits and shirts. Over the last few years, I had two suits and several shirts made to measure. It’s clothing that actually fits me like I’m a grown-up, and while it’s irresponsibly expensive, the fact that I feel like a respectable adult in it makes up for the cost. Meanwhile, owning these items has disincentivized me from a certain amount of antidepressant shop-grazing (which often gets me buying things I shouldn’t really be wearing at this age). Paul’s shirts and suits have become my new, now in my 40s, best-defended version of myself.

I don’t wear bespoke shirts every day, of course. I only have a few of them, and my actual, non-fantasy life — you know, the one where I’m not being called on to be amusing at glittering, intimate dinners — doesn’t call for it. Also, I don’t sell expensive real estate or work for Gagosian Gallery. Realistically, I try to just not provoke comments in others about how I’m trying to dress too young for my age. (As an underminer co-worker put it once: “A T-shirt with horizontal stripes takes ten years off you, right?”) Which means, these days, a uniform: these button-down shirts from Steven Alan or J.Crew (usually bought on sale), a couple of pairs of leather boots (also bought on sale, from Agnes B and Armando Cabral), mixed in with a few Nordic-spicy items from Acne (nothing of which ever seems to go on sale). I still wear my Loden Dager motorcycle jacket, which Paul talked me into buying six years ago despite my misgivings that it wasn’t “me” and which has outlasted its moment being almost alarmingly on-trend to become, more than any other item of clothing I own, probably, actually “me.” Or the me I’ve become. Then there’s that which is marketed to me that I reluctantly submit to: Parke & Ronen, for example, which all but screams “I’m trim and prosperous and gay!” And then there was my brief, possibly age-inappropriate dalliance with Surface to Air, but mostly because my boyfriend knew someone there who would give me his discount.

What I now avoid: Shorts at the office. Or striped T-shirts. And most of all, Topman and its fast-fashion ilk, not only because it’s the equivalent of dressing in a Justin Bieber song, but because it’s so badly made that within three months it’s unwearable (which might be the idea). Not an unuseful thing for a 20-year-old, but annoying for my closet metabolism. Oh, and, at this point, anything vintage. Those high-waisted old-man jeans that some kids are wearing these days only look good on actually young men.

Admittedly, there is a certain shame in not being 20- (or even 30-) something: If youth is about potential, the game in middle age is no longer about reinventing yourself but about learning to work with what you’ve got. A slightly older friend depressingly once said to me that sometime around 40 he had to “accept his mediocrity” just to keep himself from going mad. Others retreat uptown, or upstate, or, if they have the money to do it, somewhere like the Hamptons, secure from other people’s glory days. Or they go the other way: One ex of mine got his neck tattooed on his 45th birthday and still lurks, with some success, around Williamsburg’s Metropolitan bar. Some have become Radical Faeries. Others, like my brother, have decided to start families, whether by adoption or surrogacy. My bourgeois bookish-aging-hipster path is not a universal solution by any means.

Rereading this, I worry that I’m saying that we should, at some point, retreat into shameful middle age. But in the end, being gay, if nothing else, is being convinced of your good taste.

The other night, I ran into Paul at a party, and I was in a suit he made for me, which he jokingly called my “armor.” He’s right. And never have I felt more in need of such protection. It looks great because it fits me — both my body and who I’ve become.