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The Return of the Hat

Christopher Bollen finally wears one

Last winter, during a warm snap, I made a survey of men’s millinery on the streets of New York. On a walk at 11 a.m. and again on my return at 8 p.m. (different times to account for morning and evening dress routines), I monitored the number and styles of hats worn by men that I passed on the sidewalk. Hat Illustration

The temperature was in the high fifties, ideal hat weather. When I tallied my sightings, I counted sixteen baseball caps of various teams and insignias (one instructed me to buy myself a beer; another was equipped with retractable ear flaps), four felt fedoras (one decorated with a woodpecker feather), two derbies, a cowboy hat (with a brown leather band and a turquoise emblem), and a beret (kudos to that last romantic). That added up to twenty-four men in hats, out of what might have been four or five hundred, or an average of one in twenty.

That is astonishing, considering the fact that at the turn of the last century, all self-respecting gentlemen were expected to cover their heads. They did it with fedoras, newsboy caps and the occasional homburg. But where, too, were the fezzes, the bowlers, the panamas, the stovepipes, the porkpies, the Greek fishermen, the officer’s caps, the deerstalkers and sombreros?

In the early twenty-first century, at what might be the zenith of male willingness to dress experimentally, to go sartorially where no father ever dared set foot (even to hide a bald spot), hats remain fashion’s awkward outliers. Mark Twain, who was not averse to sporting a top hat, remarked, “A man cannot be comfortable without his own approval,” and there is something in this adage that applies to men’s headgear. Hats take courage to wear. On a man without confidence, fear intrudes: The hat will look too costumey, branding him the victim of trend. (Remember the cowboy hat fad of ten years ago, or five years ago, when every rising pop star sported a tilted fedora on his CD cover?)

I decided to take my study a step further. I traveled Uptown to the American painting wing of the Metropolitan Museum of Art. Here, my investigation yielded a theory. In almost every portrait of America’s founding fathers, the men posed with their tricorn hats held in hand. In the midst of a new world order, the tricorn (the brim formed a gutter to run rainwater away from the face) was a decorative flourish indicative of military prowess, and it was doffed to reveal the splendor of the hair. Only in groups and on horseback did gentlemen don their tricorns, which indicated they were a team. While hats still indicate team membership, deflecting individuality in favor of collectivity, once an accessory that rendered men anonymous, they are now an ornament that declares men (too) distinctive.

As a kid, I never wore hats. I hated group sports and loved my hair. Even in a red baseball cap, my eyes seemed marooned in shadow. But in the throes of a Sherlock Holmes obsession, I begged my parents for a deerstalker cap, which I wore around the house but never outside, where neighborhood children could see that I was obsessed with a highbrow foreign detective rather than our Cincinnati Reds.

Through my twenties, friends whose style I liked wore hats, and I admired them, but when you’re 6’3″ and frequent low-ceilinged bars, even a porkpie is a ceiling duster. But on a recent trip to Mexico City, I decided finally to give the hat a shot.

On the Plaza de la Constitución, opposite the National Palace (where Diego Rivera’s murals depict Mexican history in swarms of sombreros, fedoras, feather headdresses and hounskull helmets), sits an open-air hat shop established in 1847. Here were hats in every conceivable size, shape, material, brim width and curl. The main clientele was local, mostly older Mexican gentlemen. I sampled several hats until I found a black felt fedora with a teardrop dent on the top and a black-ribbon band. A young woman wrapped a measuring tape around my head—59 in centimeters, 23 in inches. “Large,” she said, “but not extra-large. Want it?” I hesitated. I’ve been sartorially self-duped on vacations before: that djaballah in Egypt, the gauzy linen shirt in Greece, a poncho in Marfa, Texas—none worn in New York.

The fedora was expensive, thick and solid yet soft, with a silk lining. It deserved a head that would appreciate it. “The brim is a bit long. Can you trim it?” A man performed the surgery, placing the hat on a metal base and fitting a hat-shaped metal plate over it. He cut around the brim with precision and spent twenty minutes heat-sealing the edge. It was presented in a large hatbox. The hatbox did not make it home; the fedora did.

It has been greeted by a broad spectrum of comments, from “Amish” to “trying too hard.” But what I finally learned in Mexico City is the truth: Hats look better on you as you get older. You have to do some living—and maybe some head-shrinking—for them to fit.  BG

Christopher Bollen recounts his favorite hats