I should be very straight forward about this before we begin.
I hate hats.
I love hats.
As a dude of at least mentionable style (and notable ego) my hair is of great worth and concern to me. Not in the mad sense that if one were to dare touch it or shave it, I would wreak my vengeance upon them. Rather, should I suddenly go bald by the age of 30, like a good friend of mine, there's a good chance that 60 years from now, should we not have to fight the rise of the machines or some equal struggle, I would still consider it my life's great tragedy.
As such, a hat is typically a thing that gets in the way of my be-product'd hair, crushing my coif against my scalp, only to reveal the mess it left behind, rather than a properly protected do. The Ball cap (or the Baller, as one associate once called them) is as prevalent in modern mens' fashion as the blue jean, but has, in my opinion, never risen above its sartorial station, despite some rising to prices rivaling some rather nice jackets. Flat rimmed, off-side, beat-to-shit, it really doesn't matter. These hats were never meant to go with a smart suit, lest that suit were ticked out with otherwise obnoxious glitz.
But, as a resident of the Great White North (albeit the more tropical-at-times portion), I do understand the importance, and sometimes absolute necessity, to pop on a top. What's more, prior to it being made the play-thing of an ornery feline, I preferred to be seen wearing a simple black wool fedora, cock'd at a classic Bogie angle.
So, what's workable to wear for the well-made man? Of course the above noted fedora is a go-to must for any guy with an interest in how they look. Despite a reputation ruined by the decades between now and their heyday, memories of that one awkward geek in high school who always wore one, and the (ever) encroaching world of women's fashion conquering yet another aspect of mens' style, this hairdo-defending high-headed hat persists, available at any respectable mens' store for a very pretty penny, or for the brave and the bold (and cheap) the plethora of women's styles offer a price-conscious cheat, usually offering a flat-black or pinstripe without much of a distracting (or defaming) feminine touch. Sadly, the days of the professionally fitted hat are long gone, unless you've more money than I.
(I'm inclined to stop here for today, as I'm feeling sickly and scattered. Will return with part 2: The Hairy Side of Headwear)