Largely self-taught, American-born miniaturist Edward Greene Malbone's luminous likenesses most embody the romantic sensibilities prevalent in the early nineteenth century. So great was his fame that nearly half a century later, novelist Nathaniel Hawthorne invoked Malbone's name in The House of the Seven Gables (1851) to explain the power of a miniature to conjure the presence of an absent lover.

In 1801, Malbone traveled to London, where, in the work of the leading British miniaturists, he found affirmation of his already evident stylistic move away from the small, opaque miniatures of the colonial period toward the larger, airier miniatures of the Federal era. Reinvigorated, Malbone returned to Charleston, South Carolina, and began his most prolific period. That is when he created this portrait of Mary Hooper, the daughter of George Hooper (ca. 1744–1821), who had established a successful mercantile business in Wilmington, North Carolina.

The ivory's lucent surface, emerging through veils of fine lines and pale washes, sets aglow the diaphanous neoclassical dress and delicate skin of the sitter, who engages the viewer with a relaxed immediacy. Mary’s serene expression suggests that he captured her likeness before her first husband, Alexander Schaw, about whom little is known, died in 1802, leaving her with a young daughter. In 1806, the widow married Irish-born merchant James Fleming, and the couple had a son, who died young, and three daughters. Fleming died suddenly in 1811 when, having only "a few moments previous" left the family's dining table, he was "thrown against the corner of the brick market house in town by an unruly horse."