2) Others might be interested in the discussion. Maybe.
3) Pictures are easier in the forum than in the shoutbox.
I've mentioned in other places that I am trying to dress a little differently, and part of this is a different hat. I shave my head, so some kind of cover is a necessity, and bandanas are only appropriate if I'm getting dirty.
I mainly wanted to get Revs' feedback on this, but the rest of you FTFL's are free to comment.
link gives you a better description and maybe some other ideas for hats. You should try on a few to see what really fits your face shape. I'm lucky and get away with a broad variety.
If you want to be able to pack it, get a "crushable" which means it can be folded and tucked in a bog, pocket, or whatnot.
Remember the main rules to hat wearing. Take it off in elevators, at someone else's house, touch the brim when acknowledging male friends, and lift it off by the crown when greeting ladies. ;-)
Basically, find a hat shop in your area and go try a few styles on. If it looks good on your head, it fits. Ask the person working what they think. Take a ladyfriend with you and ask her.
I didn't ask anyone. I just read up and asked my wife what she thought my face shape was. Then, bought what I thought would look good on me. She agrees.
+1 for the Tilley. At least the winter one as that's what I have for the winter rain season. Don't know about the summer ones as they look a bit out of place in the UK unless you're retired...
"I used to be an adventurer like you, but then I took a pie to the belly"
I don't try to match colors. Typically a black hat will go with anything. A straw one in summer, the same. If you are buying a lot of hats to match your clothes, you are over thinking the issue. Get a black or grey one for winter and a straw for summer. If you want a bucket, get a dark one for winter and a tan or light grey for summer.