Always wore a hat to church, womens heads had to be covered. I'll wear a knit hat in the winter when it's really cold. I'll wear a baseball cap when painting or doing something that stirs up a lot of dust.
My son wears hats, fedoras and such. Sometimes a kepi, Panama hat, he just likes them. Hard to understand, he has a beautiful head of natural curly hair but wears a buzz cut and often hats.
I doubt if hats will ever be as popular as they once were but I like hats on men. Not particularly baseball caps, but others. I have an old Stetson that once belonged to hubby's grandfather whom I believe, worked for the company. I recall growing up with a haberdashery in town-- it had been closed down yet the hats remained in the window. That fashion statement just kind of disappeared with the men from the last turn of the century as they aged.(1900's)