There's no sandal that's quite as resort-y as a pair of classic Jack Rogers. They're like a paper umbrella festooned fruity cocktail for your feet. While they scream VACATION, they're far from sloppy. A pair of Jacks (so many new styles to choose from) can pull together any resort look from beachy caftan to T shirt and shorts to breezy cocktail dress. While the sandal's roots are in Capri, they always make me think of the preppy chic vibe of the Cape and Islands --- and of the East Coast blue blood that introduced the now iconic style into American pop culture: Jackie O.