I like the Fedora, but it's too classy for jeans/t-shirt or vanilla bizcas. I think some black shoes (not necessarily dress shoes... the NB walking leather shoes I have should work), decent khakis (my Lands End ones have nice, defined line), a good pressed collar shirt with a button neck (not a full button, a polo)...
I think I may actually need an open jacket on top to pull this off, maybe a long one rather than just a waist-length one? Not a trench coat, but maybe just above the knee.
I guess I don't want to look like this guy:
Maybe this guy though... from this link:
Huh, is that a dark flannel jacket?
Anyway, casual Fedora?