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I am loving the maxidress this summer. It's loose, cool, stylish—and you don't need to fret about whether or not your legs will survive public scrutiny. Don't pick anything too gauzy, or it will look weird on dry land; an opaque jersey or cotton is good. And it shouldn't be oversize: Balance the skirt's length and volume with a fairly-fitted, not-too-bare bodice so you feel properly dressed. This is a terrific choice for hosting a party or going to one (with jeweled slides and lots of bracelets or beads), but you could also throw it on for running around town (just add a slouchy bag and flip-flops or flats).
Above: Prints are hot, and a bold florah (Tocca, $385) is a sweet way to test the waters (try a smaller pattern if you're petite). I think two colors are much easier to wear than a whole bunch.