Although best known for his portraits, John Singer Sargent was also an accomplished plein air (outdoor) painter. In this uncommissioned likeness of his longtime friend Chicagoan Charles Deering at his home in Florida, the artist harmonized portraiture and landscape, weaving the sitter into a tapestry of swift brushstrokes, warm and cool hues, and the area’s rich vegetation. Dressed in white, Deering relaxes in a cane chair with tropical foliage around him as well as views of boats and blue sky in the distance. Sargent stayed with Deering for two months in 1917 while spending considerable time painting outdoors in both oil and watercolor.