When you find a flattering dress you absolutely love (like this J. Crew wool dress, $158; jcrew.com), take it to a good tailor and have him replicate several versions in different colors and prints each season (some tailors will even provide the fabric). Wear a dramatic necklace or funky cuff to make each outfit unique.
At the Alvin Ailey Dance Theater’s benefit gala, Gabrielle Union showed up in a strapless styled Prada gown in a rich shade of emerald green. A diamond wreath at her neck and black T-strap heels completed her look.