I have a black baseball cap. It is from a skater shop but because it is all black, including the logo, I don't really look like a skater in it. I also have a wide brimmed straw hat but I look too mumsy in it so I rarely wear it.
I love my canvas wide-brimmed surfie hat. But then, the only time I really wear hats at all is at the beach or park or similar, so floppy surf hat plus sunglasses works well for me.
I am guessing you're talking sun protection style hat and not day at the races type hats here (because that's a whole different kettle of fish)?
Bookmarks