I usually wear a hat when outdoors, as a fashion statement and on the advice of my physician, who says that bald white guys either wear hats outside or are wearing a cancer farm on top of their head. Herewith a recommendation for a good line of hats and some remarks on making them.
Akubra · Speaking as a long-time and serious hat-wearer, and inhabitant of a wet climate, I can't say enough good things about the models from Australia's Akubra.
I've owned several, and currently use the two illustrated above (both in standard dark brown). The Leisure Time is a good all-around hat, sharp enough to carry off even with a suit and tie. The Territory's brim is extremely wide, too much so to be practical except when you have to be outside for a while in a steady rain or brutal sunshine. They are well-made and durable enough that I've never worn one out.
There are also some excellent hats made in Italy, more urban in style but less durable and much more expensive.
Hatmaking at Biltmore · In my youth, I was a hatmaker. During the summers of my college years I worked at Biltmore Hats, a Dickensian dark satanic mill where the employees, aside from myself, were grizzled hunched veterans of decades of hatmaking, or wasted young dope-smoking high-school dropouts. There was piecework, so if you worked hard you could take home a few bucks.
The process of hatmaking, rabbit fur to fedora, is pretty interesting, and Akubra has thoughtfully provided an illustrated description. I put in a little time on their Step 3, but really the bulk of my short career was on Step 2, which we called “coning”. If I shut my eyes I can remember all the steps in the short rhythm of coning a hat.
I was young, strong, and stupid, and while I worked there set an all-time record for the most hats coned in an eight-hour shift: fifty dozen. I don't know how long it stood or if it still stands.
It was a messy, stinking, horrible job, and every day I give thanks that I eventually stumbled across computers.