I have worn all sorts of hats over time. I used to have an Akubra, till I wore a hole in the crown, replaced it with a leather hat, which does not look anything like it did when I bought it, having developed a customised pinch, (no doubt due to my chivalrous tipping of the hat towards the ladies) Keeps the sun out of my eyes and is waterproof. However these days I am as often as not seen sporting the old cloth cap, which is "de rigeur" down the allotment and can be easily stuffed into a pocket. It also suits if you are wearing a hooded jacket. I also have a felt hat for urban wear, a bit like an Akubra, but thicker felt from Ecuador and for the cold weather a Lowe Alpine mountain cap. Of course I do not wear them all at once, although there used to be a notable local eccentric called "Jimmy" who did just that, wandering around town with several hat's one on top of the other.
My brother used to have a DIY Davy Crocket type hat, I think he made it out of a dead fox complete with skull for added curiosity.