Painted toward the end of Reynolds’s career—the artist was by now in his sixties—the portrait of Selina, Lady Skipwith, exemplifies the late, looser style of the president of the Royal Academy. Despite her extravagant hat profuse with plumes and ribbons, Lady Skipwith appears sullen, some might say even sickly. Her exaggerated paleness was a fashionable effect—in this culture, light skin was an ideal of female beauty tied to class and race—and it was enhanced by the application of makeup sometimes containing poisonous lead white. Blotches of red on her cheeks were just as fashionable: rosy cheeks, besides accentuating the ability of light skin to blush, signaled youth and also modesty. One of her gloves has been removed to expose the fair flesh of her right arm and a bracelet. A nosegay—a small bunch of flowers—tucked into her neck kerchief was a common accessory for women that provided a pleasing fragrance.

Selina was thirty-five years old and recently, though not happily, married when this portrait was painted, in 1787. She did not bear children and was widowed a few years later, acquiring the estate of her late husband, Sir Thomas Skipwith, whose ancestors had in 1645 sold plantations in Barbados, a British colony that relied initially on indentured labor and, from the mid-seventeeth century, enslaved labor. The considerable wealth of Selina's own family came from land owned in England and Ireland. She lived to be eighty years old and was remembered as a strict, formidable woman who was an avid horseback rider well into her seventies.