yeah I eat rear end posted:

In my experience you have to start out being known as a "hat guy" to pull one of any kind off. If you aren't a hat guy and you suddenly start wearing one, everyone will be like "hey what's with the hat?". Maybe if you went into hiding for a year or two and came back with a hat it would be less weird.

As for type of hat it matters more how you look than how the hat does. If you are ugly any hat you wear is going to look bad, but I think the most neutral kind is just a baseball style hat (not one of those ones with the flat brim and the sticker imho, a normal one). Feel free to add a decorative fish hook on the brim so people know you're outdoorsy.