Here they come now,winter hats, making their annual flight from the recesses of our closets to the crests of our persons. The plain-spoken stocking caps, the trapper hats, the rabbit-fur fantasia — to watch these and a hundred other designs re-enter circulation is at once to witness the most natural thing in the world and to size up something strange. Hats seem essential in frigid air, but many seem impossible to wear with a straight face, given the cultural climate. Get a whiff of the models that served our grandfathers well: They now combine the must of a midcentury hatbox with the musk of 21st-century body spray. Take a look at the grown-ups wearing wool caps decorated to the verge of doubling as stuffed animals. The impish self-consciousness of such nonsense shows that gussying up the head is, however awkward, serious business.
Donning a hat for the winter was much more straightforward a century ago. In many American cities, the 15th of September stood acknowledged as Felt Hat Day. Men discarded the straw hats that had seen them through summer and began sporting heartier replacements — a practice once enforced, in 1922, by roving mobs who snatched and smashed the straw hats of laggards, a perversion of etiquette indicating the severity of social regulation. Of course, 1922 was a long time ago — longer yet when we consider that ideas of hat etiquette extended from a millenniums-old tradition in which the primary function of the hat was to signal rank, with protection from the elements a chief consideration of only those with a very meager claim to status.
Then a casualty of casualness, hats went out, though without going away. The importance of the hat declined sharply, but its prominence could not; it’s right there on your skull, which encases a brain that maybe isn’t sure how to reconcile the desire to be cozy and the need to project a proud presence. The beret with its sensuous slouch, the hunter’s cap summoning the sputtering ghost of Elmer Fudd, the beanie that appears tossed on as an afterthought: These cannot help looking like extensions of minds making claims about who we think we are.
The simplest defense against the elements must be the woolen knit cap. It matches your go-to coat or perhaps extravagantly fails to match it, which is its own sort of harmony. Perhaps it is not worn with a coat at all, as when coddling the scalp of an Angeleno who coordinates it with well-tended stubble. It was once famous as the Monmouth cap, which connects it to the Welsh town whence it emerged. But it is also known as a watch cap, which connects it to sailors and the work-wear sensibility that so dominates the contemporary business of getting dressed. The peacoats, the lumberjack plaids, the engineer’s boots, the egalitarian affectation: The watch cap coordinates with these, even when woven from cashmere.
This is the modern standard, virtuous in its blankness — a status-neutral hat. It is the natural headwear destiny of a people who pride themselves on their freestyle pluralism and pretense to classlessness. Woven in team colors, it absorbs the functions of the ball cap. Decorated with slogans, it speaks the language of a chatty T-shirt. Pulled back so that its tip flops aside in a grunge-chic droop that is nonetheless somewhat Smurf-like, it suggests youthful insouciance. However it is worn — snug and action-star tough, or pert and go-getter jaunty, or with its cuff carefully skewed to imitate devil-may-care rakishness — it looks democratic. It is built for lying low and blending in.
Ski bums and skate rats and middle managers alike have recognized the sensibility of a variation called the chullo — the numbers with the ear flaps and the chin ties and perhaps a stalwart file of alpacas decorating the perimeter to indicate their Andean origin. That these, and their Nordic ski-wear cousins, have achieved a certain currency goes toward the multicultural character of the winter hat. Like the furry Russian ushankaor the fuzzy Afghan karakul, the chullo was smoothly appropriated into the vivacious hodgepodge of American clothing — notwithstanding the fact that pairing one with a North Face jacket or a Patagonia fleece can strike an off-note of cultural tourism, like declaring yourself a citizen of the world on the strength of receiving a guided tour of Machu Picchu.
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Charles ‘Teenie’ Harris/Carnegie Museum of Art/Getty Images
Eminently casual, the knit cap negotiates a smooth escape from the baggage of tradition. Which is plentiful, for a felt hat with a full brim carries complicated associations. The sort that looks swell when matched with the burliness of a Big Sky cowpoke and the whiskers of an Atlantic walrus is one thing: work wear repurposed to serve daydreams of dude ranches. Its urban cousins, the porkpie and the trilby and so on, are quite another. To dress up in an old-school winter hat is to risk tripping over a timeline and taking a fall.
In 2015, a fellow who sincerely wants to try something of the kind treads carefully, knowing that this is not just a hat but a statement, perhaps an unpleasant one. The fedora has become a metonym for a certain kind of geeky jerk who seizes on the patriarchal style that left Trow uncomfortable. Oldsters and dandies and dolts soldier on under them. Cool dads pushing strollers in the cold wonder if, on the model of Run-D.M.C., they have managed to make Winston Churchill’s homburg look street-smart. But mostly, men realize that the untroubled wearing of a formal winter hat has become a prerogative of women, who will be seen beneath fedoras and the like — one popular style is wine-colored and wide-brimmed and protective in its chic — unto the vernal equinox.
I have noticed a few of these revived styles on baristas in very nice coffee shops, a class of people who may collectively represent the leading trendsetters in the field of popular millinery. Encouraged by employers to cover their heads but forbidden by taste from testing the style potential of hairnets, they effectively do R.&D. while foaming milk. I sense, for instance, that the kids in the coffee shops have emboldened an increasing variety of city folk to attempt the flat cap (also known as the driving cap, the golf cap, the Andy Capp cap) and a close relation, the newsboy cap. A few years ago, the flat cap seemed, on so many heads, too much of a tweedy period piece, but now its appeal seems clear: It affords greater dignity than a baseball cap but not so much dignity as to make things awkward for anyone.
Such considerations of decorum are the heart of the matter. The person in the winter hat wants to show pride but not pomposity and is not always sure how to achieve that, the relevant rule book having been shredded. The mild absurdity of the winter hat is best expressed by the common pompom at the tip of a wool cap. This frizzy ornament echoes the tuft atop a tam-o’-shanter and, more distant, the fluff summitting the hat of a Norse fertility god. Its bobble bounces with the memory of childhood holidays, and maybe this nostalgia is like an insulating layer of cheer brightening the long nights around the winter solstice. The pompom’s whimsicality acknowledges, and seeks to defuse, the gentle embarrassment of upholstering the seat of reason.
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