Diana Sackville’s mirthful expression, windswept tendrils, and spontaneous sense of motion convey an air of charming informality. Her casual elegance reflects a general trend toward naturalism that arose in the late 1700s, largely as a result of a relaxation of decorum in high society and the fashionable negligence popularized by Georgiana, Duchess of Devonshire, whose portrait hangs nearby. This painting was commissioned by Diana Sackville’s fiancé, John Crosbie, 2nd Viscount Crosbie, who, at 24, likely valued the chic emphasis on vitality and informality in this portrait of his future wife.