johnnyreb, a lot of good observations and points here. Without getting too pop-psych, some of this may relate to many boys not being reared with a dad, or being reared with several dads with entirely different rule sets, which makes everything somewhat loose and negotiable. Hat etiquette in itself may be relatively trivial, but it signals lots of social dynamics that run deeper. It's true that caps have become the economy toupe. I still have hair on top, but often wear hats, and I have seen people look surprised to see me take off my cap and reveal hair. I hadn't thought of it, but it rings true that the ball-cap cultures (forwards and backwards) led to perpetual wearing of caps that was not related, for most guys, to any sort of manners. It's also good for me to be reminded that wearing and not wearing shoes is a point of etiquette for many people in various cultures and areas. Many households find it really rude if you do not remove your shoes; often they will help by reminding or explaining this. I associate this with various cultural groups, but it also applies in some areas. In and around New York City, because of the exposure to filth moving through the streets and subways, many people with wide ranging cultural backgrounds don't want your shoes on in the house, and after thinking about it, I say, good choice.
Any time you enter a building, the hat should come off.
