The painting depicts two young women sitting up in bed, fully dressed, each holding an infant. They are traditionally said to be sisters, although the different coloured eyes of the ladies and children show that they are not identical twins. The babies are swaddled in red christening robes.
The painting was known to be in the collection of Thomas Cholmondeley (pronounced 'Chumley'), the third son of Sir Hugh (died 1601) and Lady Mary Cholmondeley, who was an ancestor of the last Lord Delamere of Vale Royal, Cheshire. George Ormerod, in his description of the former monastery of Vale Royal (History of Cheshire, 1882, II, pp.154-5), noted 'In the passage leading to the sleeping rooms ... an antient painting of two ladies, said to be born and married on the same day, represented with children in their arms'. Although Ormerod gave detailed information about the Holford and Cholmondeley family pedigrees he made no attempt to identify the sitters in this portrait. The style of the painting would seem to date it to c.1600-10, and it might represent daughters or nieces of Sir Hugh and Lady Mary Cholmondeley; there is nothing in the genealogical tables published by Ormerod either to support or refute the assumption that the sitters were twins. They might only have married into the Cholmondeley family and the fact that they shared the same birthday could be explained as pure coincidence. Nevertheless, they share a strong resemblance.
Family group portraits of this type were popular in the Elizabethan and early Stuart periods. Traditionally employing emblems or symbols to show identity and status, they rarely offered psychological insights into the sitters. The pose is not known to have been used in any other British painting, but was frequently seen in tomb sculpture. John Hopkins (1991) suggests that the portrait may show two sisters, Lettice Grosvenor (1585-1612) and Mary Calveley (died 1616), who were the daughters of Sir Hugh Cholmondeley (1552-1601) and Mary Holford (1563-1625). The evidence is not definitive, however, and the identities of the sitters, like that of the painter, remain a mystery.
John T. Hopkins, '"Such a Twin Likeness there was in the Pair": An Investigation into the Painting of the Cholmondeley Sisters', reprinted from Transactions of the Historical Society of Lancashire and Cheshire [for the Year 1991], vol.141, pp.1-37, reproduced opposite p.1