Gabrielle "Coco" Chanel donned white cotton trousers in the days when ladies wore skirts and tanned her skin when a pale face was the height of fashion. So it is no surprise that she brought a similar rebellious streak to designing jewelry. "Chanel thought gems should show off a woman's style, not how much money she had," says Russell Zelenetz, a partner in STEPHEN RUSSELL, the New York estate jewelry firm in possession of this circa 1938 headpiece. "At that time people wanted diamonds and platinum." Instead, Chanel chose semiprecious stones—rubellite, aquamarine, peridot, tourmaline—and insisted they be set in silver. Price upon request. At Stephen Russell, 212-570-6900.