Anna Merola, 49, likes to take timeless pieces and give them a tweak. (Her charm bracelet holds no charms at all; dangling from her everyday watch is a tiny silver horn, a nod to her Italian heritage). Then there are her pearls—Merola is an assistant retail manager for Honora, the freshwater pearl importer, which gives her free rein to dress herself in strands of baroque, button, and keshi varieties, in colors from azure to charcoal (from $165 each; all, Honora). She incorporates other styles, too, like a necklace woven with denim ($450) and a ribbon-and-chain bracelet ($298; both, Camilla James). But it's the pearls that define her look. Says Merola, "The color, the texture, the sensation on my skin—they make me feel alive."
Stud earrings, Jenny Bird, $40. Smoky quartz druzy ring, Gara Danielle, $165. Headband, Emi-Jay, $6. Dress, Max Mara.