A part from a schoolboy cap I had between the ages of 7 and 14, I can only think of one hat I have ever possessed.
It was an object with earflaps. I bought it when I lived in Boston, where the winter air is for the penguins. I wore it a very few times, and recall only once test-releasing the flaps while waiting for a bus in Brookline. Not until recently have I admitted to myself why this made me decide to discard the hat forever. It was because I suspected that the hat made me look like a penguin. I thought, gosh, I'd rather have deep-frozen ears.
You may put this down to vanity.
Me, I put it down to some deeply masculine strain of wanting to appear normal. I've worn hats in amateur theatricals - but that didn't bother me because I was being someone else. I have worn a hired gray topper at a wedding, but then all the other males were similarly hatted.
But whenever I have tried on a hat in a shop, convincing myself momentarily that perhaps, after all, it would be OK to own at least one of some sober sort (a trilby like the one my dad wore, maybe, or a yuppie cloth cap - but definitely not a baseball cap), the immediate laughter of all witnesses has succeeded in dissuading me from the purchase. Perhaps it is my suspicion of the absurdity of all hats that is primary and the fact that they make me look absurd secondary.
The truth is that men's hats are peculiar items. Clearly, they have little practical use. Umbrellas are far more effective at keeping rain off you, for example. Even hats with guttering overflow rapidly.