I like the looks of the Stetson Bear Creek - a Sovereign quality c-crown fedora with color and band that would look good with casual wear. I believe it's the same shape and dimensions as the Chatham (it's on sale until Dec 26 use coupon code '$AVE12' for $20 off).
Depends on your budget. My two favorite casual wear hats right now come from two ends of the spectrum. I've got a Bailey wool felt pinch-front in brown with the brim snapped up all around that I like. A little whimsical, very comfy. They run about $40. My other favorite casual is a Borsalino Como in taupe. Not a hat most people associate with casual wear, but in taupe it looks pretty down to earth while still being a very well-made (for contemporary make) hat and very comfortable. Comos are in the $300 range.
Hi Shodan: I'm still not sure as what you call a "Dress Hat" could you post a pic or describe it? Brim width, ribbon width, bound edge, crown style, brand name ???
In my opinion a thin ribbon gives a hat a more casual look. Now, RBH may want to whack me up side the head for saying that but... I'd hope he would give me fair warning as to remove my hat first.
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