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Straw Trilby Hat
If ever there was an accessory that demanded paring with a Cuban cigar, it's the Straw Trilby Hat ($40). This classically-shaped paper straw hat sports an unassuming brown color, accented by a colorful chambray band. Wear it with a suit, resort wear, or a plain ol' tee and flat front khakis — but leave the pleats and jeans at home.
