As the maid of honor in her sister Angela's summer wedding in New Jersey, Regina says her dress by Vineyard Collection was a great choice: "Since there were 10 bridesmaids total, when we all stood together, the gray looked sophisticated but not overwhelming."
Why this dress works This neutral but stylish color, combined with a drama-free fabric and flattering silhouette, means an easy makeover for future wear. Having a pro alter it to cocktail length was an easy call—chiffon is a classic eveningwear fabric, very appropriate for any swanky event.
The dress also succeeds in its shorter form because of the empire waist and straight, loose-fitting skirt. In general, a long A-line gown might also work as a short dress, but would likely require much more in the way of alterations to make it fall correctly.
On Regina: Sequined ribbon and gunmetal chain necklace with crystals, $165, Wendy Mink Jewelry, 212-260-5298; Salvatrice sterling silver and 15-carat cubic zirconia cocktail ring, $450, donnadistefanoltd.com; Lace Leather Strappy shoes, $654, Burberry, couture.zappos.comJoel Greenberg & Wendy Stewart Photography (left), Robert Mitra (right)