After a few visits to Spain, I started to notice something curious: the old men there all dressed alike. They all wore slacks and sweaters, and they all walked with canes. Stranger still, many clearly did not need these canes — they walked perfectly well, and some even carried their cane under their arm!

What was going on? If I moved to Spain, would I, too, do the same when the time came? Was the Spanish government handing out canes and cardigans to senior citizens? It turns out I didn’t need to emigrate to get my answer. I find myself in the thick of the middle-age version.

For no good reason, about a year ago I started fancying a hat. No biggie, right? We all need to protect ourselves from the ever-harsher rays of the sun. The thing is, I didn’t want just any hat. Not a baseball cap, not a bucket hat, I wanted a trilby. A trilby, if you don’t know, is a bit like a fedora, but the brim is narrower, two inches or less, which makes it pretty useless for blocking out the sun from your eyes, or pretty much anything aside from the top of your head.

Then why a trilby? That’s the thing — I don’t know! I just got the urge, and I couldn’t shake it. Did I think it was cool? Not exactly. I mean, who in my radar regularly wears a trilby these days? I can only think of one famous example, and that’s Elvis Costello. And I assume the only people who think Elvis Costello is cool these days are middle-aged men who wear trilbies, basically a tautological argument.

Maybe it was misplaced nostalgia. Not for the 1960s when trilbies were popular, but for my cool days in the ’90s, back when I was too cool for Elvis Costello. Specifically, the year I wore a beautiful corduroy trilby that I bought at a thrift store — until I lost it (actually, I’m almost sure that it was stolen by my brother’s drip of a roommate, the one who wanted to direct silent films).

While the loss of my beloved hat wasn’t the catalyst for the end of my coolness, it did happen at around the same time. At the end of the decade I finally had to stop taking random (and infrequent) slacker jobs and got my first full-time job as a writer. Not only did I get tired of the doorman at the FiDi building where I worked stopping me to explain that deliveries had to go through the back, my editor, out of the blue, advised me one day that I needed to “stop dressing like a beatnik.” Not long after, the dot-com bubble burst and I had to find another job, forcing me to get even more serious, and I just got too busy to properly maintain my bohemian practice.

But was nostalgia really to blame? If so, I could have taken easier paths, like going to see The Pixies or Pavement or any of the other bands that were once cool but are now just trying to pay their mortgages, or listening to the Trainspotting soundtrack while sweating on my rowing machine. But I’m doing neither. Then what was making me want this stupid hat?

If it wasn’t a yearning for the good ole days, could it be… social influence? I started looking around at other middle-aged men in my neighborhood, and to my horror I discovered that a surprising number of them wore hats — not baseball caps, not bucket hats, but trilbies. Some were older and looked like they’d been wearing them before Elvis Costello got his, others were dads picking up their kids from daycare — neither group on the cutting edge, but definitely on both ends of middle age. And I’m smack in the middle.

Okay, let’s accept that I picked up the idea by osmosis. So where did all these other middle-aged guys get it from originally? Does it just happen when you reach a certain age, like how the lenses in your eyes begin to lose flexibility when you hit your 40s? And if that’s the case, what’s next? Shall I wear the bottoms of my trousers rolled? Will I find paraphrasing T.S. Eliot funny?

I wore my trilby last night to meet my friend Jason for dinner. He’s my age (well, three months younger, as he likes to remind me), and he complimented my hat. “I’ve been thinking of getting one myself,” he said. I asked him why. His response was the answer I had been searching for all along. “Because I just don’t give a fuck anymore if I look stupid.” Elvis Costello himself couldn’t have put it better.