Because it's tied at the waist and the silk is slightly sheer, this caftan (Jean Paul Gaultier Maille Femme, $795) never feels too voluminous. Although Lipton wears it over a coordinating maillot (Jean Paul Gaultier Maille Femme, $395), it would also work well for entertaining at home, perhaps with a single striking necklace (Disaya) and bare feet. "The stripes remind me of North Africa," says the well-traveled Lipton. "I'm not usually a 'statement' dresser—I'm more under the radar—but I think summer is a good time to experiment with something bold and fabulous."
Next: More great summer basics: 7 new ways to wear khakis in 2010