*tries to sigh deeply in a masculine fashion, can't. throws hat*
Hats are cool. 
I often throw mine into a room to find if I am likely to be accepted or not.
I figure that if they throw my hat back out, I am not welcome in the room.
I should probably NOT go in.
Hats are very cool.
I'm short and have a big ol' head, so I wear only knitted winter hats, as needed on cold days. 
I am not really tall (five feet, eleven inches), but I was raised to wear hats. All my uncles and cousins wore hats and there are pictures of really old guys in my family album, all wearing hats of one sort or another. I have about forty or so hats, "western" (Cowboy, if you must) hats of all possible materials and configurations, six that could only be called "English Riding" (or very fucking queer! ... depending upon your perspective), three that are similar to a turn-of-the-last-century train engineer's caps, about nine others that are more difficult to describe, made of various native materials, such as a panama from Panama (who wudda thought that you could find a really well made panama in fucking Panama) and a leather "caballero" sombrero from southern Mexico, but they are the ones I wear from time to time.
My "collector" hats are a completely different and far more involved story. I actually have every known military head cover, from the Civil War to the first Gulf War (that includes those stupid looking Coast guard things that no live male would ever don without being threatened with bodily injury or confinement), in my possession, not to ever be worn. That is more about an obsessive interest than wearing a hat, though.
I generally wear one of the hundreds of free "caps" that I own from various promotional encounters. Only a few of the many promotional caps I own, which I think of as disposable in all but about four or five cases, have I ever purchased.
Semicolon, where are you? We miss you!