Martha Wayles was the daughter of John Wayles and Martha Eppes Wayles. Her first husband was Bathurst Skelton, which died in 1768. She then married Thomas Jefferson in 1772. According to an Eppes family history, Martha Wayles Jefferson gave portraits of herself and Thomas Jefferson to her sister, Elizabeth Wayles Eppes (Mrs. Francis Eppes). Martha Wayles Jefferson died in 1782, so the portrait was likely painted between 1772 and 1782. There is a possibility that they were painted together in a double portrait, which would have been highly unusual for Virginia. The fate of this portrait is unknown.
According to a family history, “so many of the Eppington portraits and old relics are lost. Among the portraits was one of Mr. and Mrs. Jefferson, presented by Mrs. Jefferson to Mr. and Mrs. Francis Eppes. There were also portraits of Richard Eppes and Martha Bolling, father and mother of Francis Eppes, and also a portrait of colonel Robert Bolling and his wife Ann Stith.”
See: Eva Turner Clark, Francis Epes, His Ancestors and Descendants (1942): 253.
I would like to thank Diane Ehrenpreis for bringing this portrait to my attention.