Let's just get this out of way: Hats can be trouble. Unless you're already a hat guy, wearing one out of the blue can leave friends and family wondering, variously, what's gotten into you, who you're pretending to be, and whether you've become one of those hat guys.
That's the main reason why Miansai's new Panama hats are so cool (the others being they'll keep you cool and protect your head from the summer sun). These hats are loosely hand-woven in Ecuador – where, contrary to their name, the style orignated – and feature a narrow brim, giving them a touch of the rugged, while preventing them from broadcasting the sort of look-at-me affectation beloved by hat guys everywhere.
In short, they're more Bogart and Teddy Roosevelt than, say, Fonzworth Bentley. We've found they travel well and transition easily from being thrown on with a pair of swim trunks or shorts to topping off a blazer and tie. And while there's a host of color combos and an option to custom-design your own, we'll take ours natural, with just a simple navy trimming. [$95; miansai.com]