Gainsborough had known Elizabeth Linley since her childhood, before she became famous as a singer celebrated for her beauty and charm^[1]. In 1772 she eloped to France with the dramatist Richard Brinsley Sheridan, and the two married the following year^[1]. They settled in London and lived well beyond their means for some time, until Sheridan's growing success, first as a playwright and later as a member of Parliament, gave the marriage firmer financial footing^[1]. The marriage itself was not an easy one: the couple's natures were incompatible enough that Elizabeth spent much of her time in the country, where she was happiest, while Sheridan remained in London^[1].

Gainsborough seats his sitter directly on the ground in a loosely painted, light pink dress, her legs crossed and her hands clasped together, her head tilted slightly as she gazes out of the painting^[2]. Her hair, pulled back loosely, has come free of its ribbons and swirls around her face as though caught by the same wind that moves through the leaves of the tree sheltering her^[2][1]. The pose and setting draw directly on Anthony van Dyck's tradition of posing a sitter against a sweeping tree and landscape, but Gainsborough goes further than van Dyck in binding the figure into her surroundings, so that the woman reads less as a figure placed before a backdrop and more as someone who genuinely belongs within the scene^[2].

Gainsborough worked largely wet-in-wet for this portrait, layering loose washes of paint that produce a soft, unresolved quality throughout the picture^[1]. Her face is the one solid, carefully modelled element; everything else, her arms, her hands lost in the folds of dress and scarf, the transparent fabric twisting from her shoulders down across her chest, is treated with comparatively flat, minimal shading, so that the eye is drawn back again and again to her expression^[1]. Gainsborough had originally planned to add sheep to the landscape for a more pastoral effect, but did not live long enough to complete that addition, leaving the picture as it now stands^[3].