List of Illustrations Miniature portrait of Elizabeth Willing, unknown artist, circa 1760. Courtesy of Philadelphia Society for the Preservation of Landmarks, Powel House cover Portrait of Elizabeth Willing Powel, attributed to Matthew Pratt, with dating as herein considered. Courtesy of the Pennsylvania Academy of the Fine Arts, Philadelphia. Henry D. Gilpin Fund frontispiece FIGURE 1. Portrait of Elizabeth Willing Powel, attributed to Matthew Pratt and painted in 1768-1769, at about the time of her marriage to Samuel Powel. Courtesy of the Philadelphia Museum of Art 11 FIGURE 2. Memorial to E. R., a mourning portrait painted by James Claypoole, Jr., signed and dated in Jamaica in 1774. Courtesy of the New Orleans Museum of Art 43 FIGURE 3. Portrait of Ann Shippen Willing, attributed to Matthew Pratt, circa 1786. Courtesy of the Philadelphia Society for the Preservation of Landmarks, Powel House 45 FIGURE 4. Portrait of Mrs. John Bush (Charity Platt Bush), attributed to Matthew Pratt, circa 1786, in which the subject wears an invented dress similar to that worn by Elizabeth Powel in the frontispiece portrait. Courtesy of the American Antiquarian Society 46 FIGURE 5. Portrait of Madam Powel (Elizabeth Powel), by Francis Alexander, circa 1825. Courtesy of the Museum of Fine Arts, Boston 64 1 An Enigmatic Portrait SHE GAZES OUT IMPASSIVELY across the divide of more than two centuries, inviting us to decipher the coded message her portrait contains. No classic beauty, she appears in a strange setting and in clothing not easily labeled. From beneath a beehive of lightly powdered hair, her facial expression conveys a sense of muted sadness. The portrait's dimensions and elements of formal composition suggest that it represented an important commission, such that the artist who painted it would have been expected to do right by his client and her wishes. His subject, wearing a low-cut yellow dress, seems free of the constraint that stays typically imposed in portraiture of women of a certain age in the late eighteenth century.1 The dress's long tight sleeves taper to sawtooth cuffs, drawing attention to the fingers of the sitter's hands, which are interlaced in a pattern that may provide a clue to the painting's hidden meaning. A purple scarf is draped across her body. To reinforce the somber effect, the woman in the yellow dress has avoided wearing any jewelry. On a pedestal to her left stands a funerary urn whose inscription, in the canvas's darkened condition, is now barely legible: Dear Pledg/ of Chaste &/Farewe. In the immediate background looms a rock formation, and in the far distance, on the low horizon to the sitter's right, are trees, a meadow, and hills.2 How else can one interpret this enigmatic portrait except as the picture of a woman in mourning? If the dress she wears and its design are to all appearances unstaid, there is nevertheless no mistaking the urn with its fragmentary inscription and the purple scarf as symbols of grief.3 Today the painting, on generous loan from the Pennsylvania Academy of the Fine Arts, hangs in the rear second-floor drawing room of that elegant mid-Georgian structure located on Third Street in Philadelphia known as the Powel House. By general agreement it is now accepted as the work of the Philadelphia artist Matthew Pratt, depicting Elizabeth Willing Powel. Because her husband, Samuel Powel, died in 1793, a victim of the yellow fever epidemic that ravaged Philadelphia in the late summer and early fall of that year, it is also frequently assumed that the portrait shows Mrs. …