I wear the wide-brimmed Tilley hat. I'm mostly interested in keeping sun off my face.

I love these hats since you can throw them in the washer (but not the dryer) and keep them clean. You can throw them in your bag, too. Can't do that with a straw hat.

Another idea: if you see somebody wearing a hat you like, ask them where they got it. Oakland should have some nice, gentlemanly hat stores.