A knee-length silk-satin organza dress with layered hem makes a perfect Bermuda short story, $1,700, by Sully Bonnelly. Sandals, $225, by Kate Spade. Earrings, $485, by KC Designs for Fragments.
On him: full suit (not shown), $5,400, by Brioni. Shirt, $355, by Robert Talbott. Tie, $85, by Thomas Pink. Loafer, $450, by J.M. Weston. Sweater and shorts, model's own.