The spectacular brooch offered here pays homage to one of the earliest—and certainly most famous—examples of Van Cleef & Arpels’ mystery-set jewels. Upon abdicating the throne in December 1936, the Duke of Windsor went into exile in Austria as Wallis Simpson bided her time in France, awaiting the finalization of her divorce. To ease the pain of their forced separation, the Duke wished to present his beloved with a special Christmas gift. He selected a brooch designed as overlapping holly leaves: one of mystery-set rubies, the other set entirely with diamonds. Photographs of the Duchess wearing the jewel reveal its extraordinary size and the ease with which she wore it.

Lot 542’s brooch fitting, like that of its predecessor, suggests the jewel should be placed tip-side down, though when reversed it has the pleasing effect of an aigrette. Also echoing the Duchess’ brooch are its undulating rubies, forming subtle peaks possibly intended to mimic the veining of a holly leaf. Though without a diamond-set twin, the ruby leaf is overlaid by scrolling diamond baguettes, further removing it from a literal interpretation of the holiday plant and reflecting the stylistic development of Van Cleef & Arpels’ renowned mystery-set jewels.