Not long after Boston was settled, a wealthy merchant named Robert Gibbs commissioned three paintings of his young children. They are among the finest of the few extant portraits made in New England in the seventeenth century. The artist who painted Margaret Gibbs, the eldest at seven, and her brothers—Robert, aged four and a half, and Henry, aged one and a half (Clay Center for the Arts and Sciences, Charleston, West Virginia)—is unknown.
However, it is thought that the same artist created likenesses of John and Elizabeth Freake and their baby Mary (in two portraits now at the Worcester Art Museum, Massachusetts) in 1674. The artist is thus known as the Freake-Gibbs painter and is considered one of the most skilled portraitists of the seventeenth-century colonies, possessing an exceptional sense of design and an admirable feel for color. Probably trained in provincial England, the Freake-Gibbs painter worked in a typically English flat style derived from Elizabethan art, which emphasized color and pattern. As was customary for portraits at the time, the children, such as Margaret, appear like adults in pose and manner.