I have almost as many hats as I have pipes, maybe as many. My favorites are the ones with a brim all around.
My wife got me a stellar Borsilino at J.J. Hats in Manhattan, but I have others. Unfortunately, for driving, with
the advent of the headrest, the brim all around doesn't work and bumps the headrest, so I have taken to more
often wearing driving caps of several kinds -- herring bone, checked, khaki canvas, black, etc. I have a lot of
ball caps -- White Sox, a cow manure cap, Subaru, Corona beer, etc. A lumberjack check ear flap hat, a Turkish
fez, a beret, and so on. The driving caps win because when I wear a hat I often drive. Also, they fold up and go
in an inside pocket and don't get lost. Hats go best when they don't look like they're being worn, or don't make
you aware that they are. They ought to look like they are part of a person's clothing and fit in pretty
seamlessly. I agree the "real man" b.s. ought to be irrelevant, at least on the hat subject. We have to work on
our humanity, and assume the gender bit will follow as appropriate.