This Wall Street Journal article makes me wonder if hats can ever truly come back.
I live in the Southwest - an area that should be prime hat territory due to its sunshine and the threat of skin cancer - and yet the hatless trend continues. Baseball caps, of course, are fairly common but they don't look good on all people - I turn into Jonathan Winters imitating a coach - and cannot be worn with a business suit.
The baseball cap also carries a touch of adolescence. Unless an adult is a baseball player, wearing a cap seems to be some fruitless effort to be young. The photos of those crowds in the baseball stadiums in the forties and fifties reveal men wearing fedoras and other "grown-up" hats, not caps.
It may be that the national desire to seem younger and to reject one's age was the real cause of the decline of the hat. If the hat returns, it may be a sign that we are changing our attitude about age.