This portrait was commissioned by Sir Kenelm Digby after the premature death of his wife in 1633 as a posthumous tribute to her. A celebrated beauty, Venetia Stanley was said to be the mistress of Edward Sackville, 4th Earl of Dorset before her marriage, a rumour which contributed to her unfounded reputation as a courtesan and probably led to the couple marrying secretly (probably in 1626) against his mother’s wishes. During the marriage Venetia was a loyal and devoted wife, and a devout Catholic. Her death was treated as suspicious at the time and an autopsy was carried out. The cause of death is still a mystery, but she may have died as a result of drinking ‘viper-wine’. Sir Kenelm Didby was distraught and mourned her death for many years.

In this allegorical portrait conceived by Sir Kenelm as a commemoration of his wife’s best qualities Lady Stanley is depicted as Prudence. The snake in her right hand is associated with wisdom, while the doves in her left hand symbolise innocence. By placing her foot on the cupid Lady Stanley demonstrates the triumph of Chastity over sensual and erotic love, while the figure of Fraud chained to one side symbolises the triumph of constancy and truth over deceit.

This picture is an important early copy of the original picture which is now in the Palazzo Reale, Milan. According to Bellori, Van Dyck was said to have been so pleased with the composition that he painted another smaller version, with some modifications, which now hangs in the National Portrait Gallery, London. The Royal Collection painting does not seem to be by Van Dyck himself, but was probably executed in his studio.