I have been wearing hats since I was kid. Still have some of them as remembrances of the good old days. I was wearing a knit wool Dress Gordon tam winters in the early 80's before I even knew I had scottish ancestry---just liked the look and warmth better than the typical watch cap of the day. Still have it, but don't wear it anymore as my head has grown some in 25 years.

Now that I am balding, about the only time I don't have a hat on is when I am indoors----keeps the sun off in the summer and the heat in in winter, and the rest of the year it is probably just habit. I have fedoras, tams, flat caps. fishing hats, ball and golf caps, bike helmets, do-rags, cycling caps, balmorals and glengarry, and my first Caubeen a couple months ago. Sorry Jamie but I will leave the pith helmet monopoly to you, although I did used to wear an aussie side snap hat for a couple summers.

I think hats are a style sort of thing---either you like them for the little bit of flair they add to your look or you don't. Seems like most folks tolerate them for specific situations or events but otherwise ignore them as a daily fashion accessory.