The end of another winter is approaching, which in my view offers many reasons for joy but one for regret. It is a reminder that despite the opportunity presented every year, I have yet to solve the perennial problem of the hat.
Anyone in an intemperate clime who has good sense knows better than to step outside on a January day without some sort of covering for the noggin. When the temperature is struggling to reach double digits, the snow is falling horizontally, and ice coats every visible surface, going bareheaded is about as sensible as going barefoot.
I found out the hard way shortly after moving to Chicago one winter many years ago. Like other baby boomers, I grew up in the years after President Kennedy made hats deeply unfashionable by refusing to wear one. The only ones I owned were caps advertising fishing tackle or farm machinery, suitable only on a boat or a softball diamond. I thought I needed a real hat like I needed a pocket watch and a monocle.
But one frigid February afternoon, I set out across the Michigan Avenue bridge on an errand. Halfway over, as the wind drilled icicles into my skull, I had an epiphany: JFK would have worn a hat if it was the difference between life and death. Having barely avoided a fatal bout of brain freeze, I resolved to buy a hat and wear it.
I did, and it warded off hypothermia until the arrival of spring. But I wasn’t happy about it, for the simple reason that in our time, it is impossible to wear a hat without looking like a dork.
This is one of those problems that rouse my conservative instincts. In the old days, when we paid heed to centuries of accumulated wisdom, Americans understood the value of hats. But in the liberated atmosphere of the ’60s, people jettisoned many traditional customs simply because they were traditional customs. Hats were seen as a suffocating imposition on our freedom to uncover our heads.
Today, we find ourselves with a far more oppressive constraint — the chilly grip of fashion, which gives scant weight to considerations like comfort and health. In a world in which hardly anyone wears hats except for reasons of necessity, they radiate homely, unhip practicality. Even Brad Pitt, who recently did a photo shoot wearing various hats, couldn’t make them work. So someone living in a wintry clime can look stupid and be warm, or look good and suffer.
If you’re a grown man who wants to protect his skull from the elements, your choices are like the dining options at a maximum security prison: All so bad that you may prefer to do without.
There is the old reliable knit stocking cap. It looked good on you when you were 10 years old, and it still looks good — on 10-year-olds. If you wear it as an adult, people will assume you just got back from a lengthy ice-fishing trip in northern Minnesota. There is the baseball cap. Nothing can beat it for conveying maturity and professionalism except maybe flip-flops and a Hawaiian shirt.
There is the fur hat once favored by members of the Soviet Politburo as they reviewed parades of missiles in Red Square. It once had a certain cachet, suggesting you were a formidable person with the means to invade Hungary if provoked. But when the Berlin Wall fell, this headgear became as obsolete as Lenin’s corpse.
There is the beret. It’s fine if you’re French, or if you’re taking a painting class at the local Art Institute. Otherwise, you might as well wear a sign around your neck with the words, "Beware of pretentious twit." Equally lame are cowboy hats, which are permissible only for someone riding a horse, watching a rodeo or going to a Halloween party.
There is the driving cap, which brings to mind a New York City cabbie, circa 1955 — something even New York City cabbies don’t want to emulate. While a fedora looks great on Humphrey Bogart in the old movies, these days, it’s the fashion equivalent of your father’s Oldsmobile or maybe Packard. If you’re a rabbi, you can get away with it. Otherwise, not.
I’ve tried most of these options only to feel deep embarrassment in every one. So from now on, I’m wearing a ski mask. Sure, I’ll look ridiculous. But no one will know it’s me.