This picture forms one of the ‘Windsor Beauties’ series, a set of eleven portraits of celebrated women at the Restoration court painted by Sir Peter Lely. The series was apparently commissioned or at least assembled by Anne Hyde, Duchess of York, probably around 1662-5. Pepys recorded on 21 August 1668 that he ‘did first see the Duke of York’s room of pictures of some Maids of Honour, done by Lilly: good, but not like.’ By describing the pictures as ‘not like’ Pepys is alluding to the often noted opinion that Lely flattered his subjects, and gave each portrait a similar languorous and ‘sleepy eyed’ air, said to have been influenced by the features of the noted court beauty Barbara Villiers, Duchess of Cleveland (RCIN 404957) who was painted many times by Lely. Contrary to Pepys’s assertion, only one of the sitters, Frances Teresa Stuart (RCIN 404514) actually held the position of Maid of Honour in the Royal Household. Some of the others were noted courtesans, while others were respected members of the nobility.

In 1674, after the death of Anne Hyde, the pictures were hanging as a group in the White Room at Whitehall which was reported as being 'Hunge wth white sarsanett [sarcenet - a soft fabric, usually of silk], and over it blew Mohair with silk fringe'. Eleven pictures are mentioned in this inventory, although ten today are identified today as belonging to the group. The series was taken from Whitehall to Windsor, presumably by James II and hung in the Princess’s Dressing Room. In the reign of Queen Anne they were hung in the Queen’s Waiting Room and later in the Queen’s State Bedchamber. They were at Hampton Court by June 1835.

All the portraits in the 'Windsor Beauties' series appear to be wholly by Lely’s own hand, except this portrait of Anne Digby, Countess of Sunderland which is probably a studio copy, after the original portrait at Althorp which is inscribed with the date 1666. Anne Digby was the daughter of George Digby, 2nd Earl of Bristol. In 1665 she married Robert Spencer, 2nd Earl of Sunderland. Her husband assembled a fine collection of female portraits by Lely which is still at Althorp.