Tip from O Creative Director Adam Glassman: Mix menswear-inspired pieces with feminine glamour—think cocktail rings, shoulder-baring tops—for the most modern look.
Dress, BCBG Max Azria, $428, BCBG.com. Earrings, $130, Emitations.com. Pins, Ban.do, starting at $55 each, ShopBando.com. Scarf, Ann Taylor, $68, AnnTaylor.com. Necklace, Glamourpuss NYC, $475, Glamourpussnyc.com. Onyx cocktail ring, $129, Emitations.com. Pearl ring, Whitney Stern Jewelry Design, $299, HenriBendel.com. Mini bead bracelets, Lisa Freede Jewelry, starting at $138 for set of eight, LisaFreede.com. Coral-colored-stone bracelet, Maurices, $22, Maurices.com. Shoes, Cole Haan, $248, ColeHaan.com.