Rule #1 - Hats are outdoor wear. That means you need to co-ordinate them with your (over)coat (especially important for a winter hat).
Rule #2 - Hats are outdoor wear. That means you take them off indoors. At the very latest, remove it with your overcoat. Preferably, remove it as you come through the door. Even talking to someone at a reception desk while wearing a hat just looks & feels wrong.
Rule #3 - Hats are outdoor wear. Anywhere that isn't air conditioned is outdoors. London Underground Train? Outdoors. London to Leeds mainline train? Indoors. Act appropriately.
Rule #4 - Remove your hat when speaking to a Lady.
Guideline #5 - Your hat does not need to exhibit symmetry (in angle, facing, crease, brim, hatband/puggaree or even colour). Like most ties, and like the pocket square, a certain level of style relies upon asymmetry.
Originally Posted by AdamWill
bourbonbasted: I guess I tend towards the costume-y side of things; my attitude is pretty much 'I like hats, so I'm gonna wear hats, and screw you'. I think a lot of the time it comes down to where you live, as well. I live in Vancouver, and moved here from England. You'd think I'd feel more sensible wearing a hat in England, but funnily enough, just the opposite. England is as prickly about clothing etiquette as it's ever been, it's just that the etiquette has changed, and now if you wear a hat, you're being pretty weird and people are going to laugh at you (whereas 50 years if you *weren't* wearing a hat, you'd be in trouble)..
How long have you been gone? Because hats seem to have made a definite comeback. This is probably not unconnected to the last three winters having been, in various ways, absolutely foul. As an example of how foul, it's April and it's still bloody snowing.