Editor’s NoteWe’re men.  Our style is portrayed less through flash and “glamour” than it is through simplicity and functionality.  The hat isn’t a tool for us– a cop-out, a cover up, it is a form of expression equivalent to the most front-facing features of our wardrobes.  We wear our hats proud on our heads because they symbolize quite deeply something about who we are– they are our calling card, our best foot forward, our Sunday Best when a fashionable push comes to shove.  To celebrate the Hat and the Modern Man, we introduce StyleCrave’s weekly style feature by our latest addition– Mr. Simon Crompton.

I started to lose my hair early, from a young age.  Therefore, I needed something to cover my head in cold weather. As a teenager the default choice was a beanie. The black, cheap variety I wore may have had Metallica, Pantera or the name of a similar metal band emblazoned across the front.

In university, the beanie remained but was usually in the rowing club colours or something similarly collegiate. Headwear had not really evolved; it just switched allegiances. There was a brief fling with peaked beanies, which seemed a little more cutting edge somehow. But it was a shallow revolution and short lived.

The real problem came when I joined the working masses and began commuting to an office every day. A beanie was passable on the train, with an overcoat and gloves. But it looked rather ridiculous with a suit and would often be removed a few blocks before I got to the office. Professional it was not.

If the beanie (or probably baseball cap in the US) is the archetypal head gear of youth, it’s adult equivalent is the brimmed hat – the Fedora, Homburg, or trilby, depending on your preference. But you can’t wear a Fedora seriously until you are at least into your forties. Along with braces, cravats and pipe-smoking, it is one of those accessories that has so many associations with an older generation it is almost impossible for a younger not to look ridiculous in.

(As an entirely subjective aside, I would suggest that the appropriate decades for begin to wear each of these items is your thirties (braces), forties (cravats) and fifties (pipes).)

Between a beanie and a trilby

So if you’re too old for a beanie (or baseball cap) and too young for a Fedora (or trilby) what do you wear? This is not an idle question. It is one that has frequently left me stuck between ridicule and a cold place. A very cold place: the hair on my head has run away at ever-greater speed since those Metallica days.

The answer, I believe is the flat cap. But not just any flat cap.

Let me explain. The flat cap in England is normally made of tweed or a rough wool. It was traditionally the default headgear of the working class and still has associations with northerners, grounds men and those who breed whippets. A few years ago, though, it enjoyed a brief renaissance and was, however briefly and haltingly, cool.

As a result I see young men regularly wearing them as an alternative to a beanie, and even wearing them with a suit to the office. Several of the best online commentators and bloggers on men’s style have also endorsed the flat cap as the bridge between the beanie and the brim.

I agree, up to point. As with everything associated with dress wear for men, there is much to learn from traditions and how they were established. A hat was considered more formal the darker, smoother and stiffer the material. Hats worn in the city were usually black or a dark grey, with brown suggesting the country. Rougher materials like thick felt were also more casual, as was a brim that was unbound (so floppier, bendier).

The same guidelines apply to a suit: worsted navy is smarter than grey flannel, which is smarter than brown tweed. Each is paler, rougher and spongier than the last.

This principle need only be applied to the flat cap to produce the working hat for the modern man. Make it dark (black or grey), make it smooth (felt not tweed) and make it stiff (again, a felt cap fits nicely). A cap of this sort is completely removed from any associations with labourers or whippets. It is the hat of the modern, office-bound man.