The city trilby, in graphite gray.  Notice the hat band's reflection--bright and noticeable, even though this one matches identically the felt. — The *city trilby,* in graphite gray. Notice the hat band's reflection--bright and noticeable, even though this one matches identically the felt.

Hats that can plausibly be worn are relatively few considering the vast array. By plausibly, I mean both without attracting unwanted attention and, more importantly, without ironic intent. This isn’t so surprising, really; a hat and one other key accessory is often all that’s required to convincingly evoke a well-known film or literary character--useful on occasions for which a costume is expected, but problematic the rest of the time. Put another way, if you do not wish to attract Guy Fawkes references, a black, wide-brimmed stovepipe hat is out of the question—even without the d’Artagnan beard.

But costume hats are hardly alone in attracting attention. Consider the bowler, which on its famous features alone should be the easiest headgear for a man to adopt. It is compact, free of immodest swoops or creases, practical in that it is stiffened. It is also impossible to wear without eliciting remarks. The same is only slightly less true of the homburg (the hat made famous by Anthony Eden and Poirot), and the top hat is largely irrelevant; the boater (a thickly plaited straw hat with a flat top and brim) is feasible, although comments involving Gatsby are inevitable, whereas the pith helmet (a military monstrosity made from tree bark; see Michael Caine in Zulu) is of course purely costume. While few might bemoan the loss of these and others, the very idea that a number of shapes have traversed from wide use to obscurity illustrates the point: the hat world is shrinking. What’s more, the phenomenon is infectious; just the other day I had to frown and shake my fist at a group of high-schoolers who heckled me for wearing a flat cap. If this everyman’s cloth hat isn’t immune, what is?

Strangely, the classic felt fedora shape goes relatively unpunished. But, and I really must stress the point, proportion is absolutely critical. Over the past several years, and with the expert guidance of Chicago’s inimitable Optimo, I have homed in on a style that seems to suit me. It is a trilby, which is to say a less exuberant fedora, with a lowish crown, wide-set pinches that sweep back somewhat, a narrow ribbon band and a brim not more that an inch and seven eighths. If this all sounds rather particular, it is; hat personalities have very little tolerance for variance, and what seem like slight changes in volume, height and placement can dramatically alter the effect. This is just how it goes when something is worn so near to that most important signifier of person—the face. Consider eyewear.

I think of the result as a “city trilby,” a sort of casual hat with country origins that has spruced itself up for a night on the town. The style handily goes from denim and waxed cotton jackets right through to suits and overcoats. In fact, so versatile is the shape I frequently envision it in several colors and finishes. But here, I’m afraid, is where things can rather quickly go pear-shaped. A shade even one increment in the wrong direction can throw things off considerably. Oxblood sounds good, but is hazardously near plum, which, whatever anyone might argue, is purple. Browns are safe, but make certain the shade doesn’t wash out the complexion. Black is a characterless vacuum and the least flattering of all hat colors. Charcoal and navy are infinitely better. And then there is the hat band. Because they are made from silk grosgrain, bands reflect rather than absorb light, the effect of which is conspicuousness. Like a tie, they gleam, so be on high alert when selecting one. I avoid bright, colorful and dramatically contrasting hat bands, opting instead for muted and dark bands very near in tone to the felt body.

Ultimately, a hat is going to be noticed, and so any further gilding is not just unnecessary, but unwanted. This is, perhaps, why many men have dropped the hat in favor of accessories like novelty socks; fine-tuning headwear is just too damn difficult, whereas an explosive item worn mostly out of site is an easy and safe way to suggest effort has been put into one's clothes. How misguided; the richest moments of personal style require not just thought on behalf of the wearer, but the audience.