I’ve been wearing hats for about 40 years. Back then they were chiefly of the fishing hat or ball cap variety. I did wear a western hat to my senior photograph session in HS. They wouldn’t let me wear it for the photo but I did wear the colonel tie. Today I have 50 or more hats/caps in straw and felt and woven fabric. I’ve worn one to each of the Free Republic gatherings in DC. (1998 March for Justice, 2001 Inaugural Ball, the event a couple of years ago in Arlington VA)
When I’m not inside I’m in a hat of some type. I have a water proof fedora 100% wool that’s at least 15 years old. I call it my rain hat. Still as good today as when new.