I've been a hat wearer for years, from long before I started losing my hair.
A Panama looks good in warm weather. Check in golf equipment and supplies stores for Panama-style hats in lots of colors.
A good Fedora or Trilby is nice to have in cooler or cold weather, keeps your head warm and looks sharp.
I have a gunmetal blue beret, the closest color I could get to Infantry blue, that I wear in cold weather sometimes. For really cold I wear a thick black knit watch cap.
And then, of course, there's the ubiquitous baseball cap, in various colors and materials, for general running around in all seasons.
.............
AJ, my sympathies. Every time I see Adam dorking around on that Segway I think, "It ain't that far, geek! Get yer ass off that thing and walk!"
![grin =D](http://www.armedpolitesociety.com/Smileys/default/grin.gif)