The gently twisting hands of the sitter, the background of vines and the presence of hatched underdrawing suggest that this portrait dates from early in Holbein's second visit to England. William Reskimer (d.1552), who came from Cornwall, as the later inscription on the drawing records, held a number of minor positions at Henry VIII's court, among them Page of the Chamber. In 1543 he was granted keepership of the ports of the Duchy of Cornwall and in 1546 was appointed Gentleman Usher. The sitter has been identified as William rather than his brother John (who also held positions at court) due to the provenance of the painted portrait, which was presented to Charles I by Sir Robert Killigrew, a direct descendant of William.

The painting shows Reskimer against a background of vines, with his right hand in an awkwardly cupped position in front of his long red beard. A comparison of the preparatory drawing (also in the Royal Collection) and painting shows just how closely Holbein followed the former; here the painting deviates only marginally in the contour of the inside of the earlobe, and even such details as the fine lines around Reskimer's eyes and the shadows on his cheeks follow the original drawing. As with the portrait of Guildford, the drawing was probably transferred to the panel by tracing the outlines with a stylus. The original drawing, however, does not include Reskimer's hands, which with infrared reflectography show clear signs of freehand underdrawing and hatched shading. The only separate studies of hands that we have are those of the hands of Erasmus. Holbein may have worked from a separate study, perhaps tracing the hands and then reinforcing the traced lines with freehand drawing. Derick Berck holds his hands in the same position, one cupped behind the other, in his portrait of 1536 (Metropolitan Museum of Art, New York), though viewed from a different angle.

Catalogue entry adapted from The Northern Renaissance. Dürer to Holbein, London 2011