This is aimed at the guys, so women, please don't be offended.
When I was younger, I really dug wearing fedora-type hats. I golfed with my dad, and would buy cheap fedoras from the convenience store (yes, they used to carry them!). As I got older, the only hats I would wear -- and then only rarely -- were baseball hats. Oh sure, when I'd go running I'd frequently wear a running cap, but I find baseball and running caps too casual for everyday wear.
Now that I'm nearing retirement age, my hair has become thin and flyaway, and I'm looking for some decent headgear for the winter.
I wear brown and black jackets primarily, and therein lies my conundrum: most fedoras I've viewed online come in black, brown and grey. I'm thinking of something in a forest or olive green, that would go with either color. And those are hard to find! I'm also not looking to spend more than $100 (ye gods, I saw one hat for >$700!). I've been looking at online hat purveyors, and thinking today is Black Friday, might find something. But price is less important that finding a good hat.
So, what should I look for? Brand? Crushable? Material (wool is preferred)? Suggestions?