Standard flat cap in handsome glen check.

Like any hat-wearing man, I cycle through preferred shapes and configurations, favoring some, suddenly rejecting others. Proper, full-sized fedoras appeal to me, but the reflected image is always slightly too near costume to have one made (even though I am confident Chicago's Optimo would nail the proportions). In the same breath, I must admit I own the ultimate costume piece: a bowler, which strikes at the very core of masculine affections for headgear as a dashing, semi-formal stiffened helmet. Sadly, bowlers are impossible to sincerely wear. Trilbies are flattering and rakish, though and I’ve long wanted a soft Tyrolean, decorative rope and all.

Linen cap folded and ready for a patch pocket.

But it's the humble flat cap that I reach for most often. Like a bowler, the appeal has a duality born of action and style. Unlike the bowler, though, the cap is a laborer’s hat—an inexpensive, straightforward design that can be deployed in an instant or folded and jammed in a jacket pocket as need arises. The cap was borrowed by well-dressed gentlemen at the turn of the previous century as a casual, sporting alternative to the (often quite literally) stiff formal hats of felt expected of the upper classes. I say borrowed because to this day the best versions are hardly made of scrap cloth; the shape might remain true to its modest origins, but the materials have moved up in the world.

Caps can be made of virtually any cloth. One of my favorites is very fine linen lined with etherial mesh made by London’s Lock & Co. As much as I depend upon my trusty straws, this is the head covering of choice when traveling. I have held cashmere caps that caused me severe internal conflict; this simple shape so beautifully rendered had the same paradoxical charm of a dinner jacket made of some rugged tartan. But tweed is really the correct cloth for a cap. If a technical fabric-swathed disbeliever ever needed proof of the original performance cloth’s ability, I would encourage the wearing of a proper tweed cap for a week. If his head doesn’t remain dry, warm and comfortable for the duration of the trial, I’ll eat my hat.