I go everywhere in a brown felt broad-brimmed fedora with cowboy hat aspirations. Since I had a basal cell cancer carved off my chest some years back, I'm interested in keeping the sun off my head. Also, there was a time decades back when a gentleman did not go outside without his hat; I wouldn't mind seeing that trend return.
I wear hats more lately because I've found some styles that flatter me which are affordable. Whatever is being sold now just works better with my face than styles in the past.
I have a black fedora, a straw fedora, & a big floppy hat. I also have a black bowler hat, but it's a little big on me. I have a newsboy cap, but I never wear it because it's not that flattering.
Cap & beanie styles tend to look stupid on me. I always liked those little knitted beret hats some girls wear, but it looks funny on my head. I like those cloche hats from the 20s, but I have a feeling they'll look off on me too... I also want one of those fur Russian hats; I don't even care if it looks dumb (to other people) .
I've never cared much about what other people wear (as far as limiting myself because of it), and appropriateness is second to what I feel like wearing.
Similar hats to mine:
(except mine is striped tan & black)
"Charlotte sometimes dreams a wall around herself. But it's always with love - So much love it looks like everything else. Charlotte Sometimes - So far away, glass sealed and pretty." - The Cure