As collectors go, the Duchess of Windsor—a.k.a. Wallis Simpson, the American-born divorcée for whom King Edward VIII abdicated the British throne—didn’t miss a beat. Her jewel box contained something from virtually every legendary maker of the 20th century, from Belperron to Van Cleef. “What she had instead of art on the walls was art on her body,” says Judith Price, president of the National Jewelry Institute. “This was the jewelry of a queen”—literally, in the case of the pearls the duchess wears in this photo. One strand is cultured. The other, however, is a natural pearl and diamond necklace by Cartier that once belonged to Queen Mary. It made history when it was purchased by Calvin Klein for $733,333 in the landmark April 1987 sale of the duchess’ jewels at Sotheby’s Geneva. The piece resurfaced at Sotheby’s two decades later, when it brought $3,625,000, reflecting not only the value of provenance, but also the duchess’ pioneering legacy. “Jewelry auctions were not the same after that 1987 sale,” says jewelry historian Joyce Jonas. “It was a turning point.”