I was in a teaching situation one time where boys wearing baseball caps indoors were one of the pet peeves of another teacher. Needless to say, all the boys would test every teacher, knowing full well that the rule was that it had to be off indoors. I listened to the kids talking one day and realized that they were very sensitive about "hat hair," especially if girls were around. (Hat hair is the ridge that shows in your hair when you've been wearing a baseball cap.)
I love it in the South when I meet a man on the sidewalk and he smiles, nods, and touches or tips his hat. This is a nice custom that we don't see too much in larger cities or out of the South.
Once my husband bought a big cowboy hat in Denver, then had to fly home by himself. By the time he got to Louisville, he was the only person with a cowboy hat on. One little kid said to his mom, "Look! A cowboy!"