Often hailed as the father of American portraiture, Stuart is best known for his portraits of George Washington, one of which famously adorns the dollar bill. Born in Rhode Island, Stuart trained in London under Benjamin West and worked in Dublin, New York, Philadelphia, Washington, and Boston. Stuart’s straightforward style of portraiture downplayed opulent dress and grandiose settings in favor of bust or half-length figures set against neutral backgrounds. His goal was to bring out the inner life of a subject through expertly layered colors and energetic brushwork—“short and chopping strokes,” in Stuart’s words. Little is known for certain about the sitter for this portrait, although new information suggests it may be a preliminary study for one of Stuart’s portraits of Lady John Temple, a member of the Bowdoin family and a prominent Bostonian.

Stuart was a study in contradictions: he was an extremely prolific painter, charming and socially connected, but he left many works incomplete, died bankrupt, and was buried in a public cemetery. But while the word “unfinished” sometimes has a negative connotation, this is not the case here; this portrait shows Stuart’s uncanny ability, praised in his own time, to capture a sitter’s personality by depicting only his or her face.