The Montego Bay is the kind of classic fedora that looks at ease anywhere the water is warm – a marina, a poolside lounger, the back nine. Set it beside my Classic Fedora, and you will spot the difference in profile: it rides taller in front and dips lower behind, and the “island” up top trades a little of its teardrop for a sharper diamond. Rumor has it that a pina colada under the brim improves your odds of catching the green flash at sundown. Worth testing. It also wears well with a skinny brim.
