Giorgio Armani ($295), giorgioarmani.com. Photograph by Brad Bridgers.
In the late seventies, an up-and-coming Italian designer was asked to create Richard Gere's wardrobe for American Gigolo. The slouchy, sexy, wearable suits he invented revolutionized men's tailoring, made the film a sartorial sensation, and turned Giorgio Armani into a household name. Thirty years later, Il Maestro, as he's known in Italy, is still applying his signature aesthetic to everything he touches, like these sunglasses. They bear the Armani hallmarks of sophistication, modernity, and universal appeal—which means you'll look good whether you're wearing them in Connecticut or on Capri. Courtney Colavita