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That's a tough call--they both look good on you.here are my two new hats. An Optimo Milan Straw Teardrop Fedora and a Stetson Benchley in beaver fur felt. Brim on the Optimo is 2.5" where the Stetson is 2". Crown is a little taller on the Optimo. Liking both hats but think the Optimo might be a better shape for me. Opinions welcome.