Robert Bolling II was a son of Robert Bolling and his second wife, Anne Stith. He was born at Kippax and married Anne Cocke. However, Robert Bolling II died before Wollaston arrived in Virginia in ca. 1755. The body and composition look like Wollaston but the face displays more modeling than usual. The portrait could be postmortem, a copy of an earlier portrait, and/or overpainted. Wollaston copied earlier Randolph family portraits and this portrait is similar in style. The portrait descended in the Bolling family in Petersburg. It may also represent a different Bolling family member.
Dimensions: 34 7/8 x 27 3/4 in. (88.58 x 70.49 cm.)
The subject wears a long white or gray wig. His left hand is in his waistcoat. He wears a dark jacket and waistcoat. His right elbow rests on a stone plinth.