A new take on '50s fashion is right at home at a funky West Side diner. Two-tone Chantilly lace ballerina-length dress with sage-green silk dupioni draped sash, $2,310, by Christos. Austrian crystal-and-pearl earrings, $165, by Jose & Maria Barrera, available at bergdorfgoodman.com, 888-774-2424.
On him: Suit, $4,155, and tie, both by Brioni. Shirt, $275, by Etro. Glasses, $180, by Christian Dior.