I seldom wear a 'cowboy' hat anymore, though I mainly did when fly-fishing. I almost always wear a boonie hat outside, but often a ball-cap. Still have and wear the Phoenix tactical cap. I've wanted to get a true Stetson for a lot of years, but ability and opportunity haven't met yet.
In the winter (we have that BIG up here) I'm always wearing my Sheepskin hat that my grandfather gave me over 30 years ago. And it still looks and works like new. A LOT to be said for 'natural' materials, right there.
Thing is though, every time I read this thread title on the main page, the 'next line' keeps popping into my head:
"Who's got their boots, dusty?"
(bad song from the 80's, now it'll rattle around in your head too. )