Do you usually wear a sport cap?

To the best of my knowledge and travels, this is mostly an American fashion. As an American who apparently can pull off (heh) most hats, I have never to my recall ever purchased one. I try them on all the time, and almost bought a sweet, quality subtly plaid flat cap one time I liked it so much, but my practical side and minimalist fashion sense (jeans/t-shirt) won out. Something to have to fuss with indoors, "hat hair" etc.

Not to say I don't *have* several kinds of hats, all "schwag" given to me by companies I've worked with that aren't too "logo-y." All worn out of utility, rather than fashion. The only time I wear a baseball hat is when I have to run out the door for a quick errand and can't be f'ed to deal with my hair.

I also have [two] olive drab Boonie hats that are all floppy and can be stuffed in to a pocket/bag for sun protection, i.e. beach/desert/sunny outdoors for long periods. And of course, when in cold climes, I have a few different winter hats, my favorite a wool one having been knitted and gifted to me by an old boss.

Damn, just remembered one time I did buy a nice but affordable Panama hat, but I wore it for outside work a little too often and used it up. So there.

Only when I go out, and for a specific reason.

I have long hair - it's a mess in the morning. If I have to go out, rather than going thru all the trouble of fixing it, I wet back the sides, and throw a cap on backwards.

Well I play baseball, or a FEDEROA

I am bald on top and like to keep my remaining hair short, but I often neglect to shave it, so I'll just throw a hat on if I have to go out into the world.

If I can't wear a hat, then I'll get around to shaving it.