Existing research on the female characters in Oliver Goldsmith’s The Vicar of Wakefield (1766) has indicated the ways in which they contribute substantially to the novel’s narrative complexity, multifaceted exploration of morality, and its socio-political contexts. Especially comparative readings of the Vicar’s daughters Olivia and Sophia have resulted in considerations of eighteenth-century womanhood and gender norms. This presentation aims to add to these accounts by providing an in-depth study of both the major and minor female characters in the novel. As its point of departure, it will show how the daughters serve as the main focal points for the novel’s conceptualisation of female virtue and sexuality. The juxtaposition of their characters, their actions, and their ideas on love and matrimony—with Sophia seemingly embodying sense and purity, Olivia sensibility and transgression—facilitates an exploration and deconstruction of the dichotomy between virtue and sin. Attention will also be dedicated, however, to the minor female characters to indicate how figures such as Mrs. Deborah Primrose, Miss Arabella Wilmot, and Squire Thornhill’s hired prostitutes embody alternative female moral types, thus complicating the dichotomy even further. Embedding the discussion of these characters within a wider context of literary-historical constructions of femininity, this presentation will explore how Goldsmith participates in a contemporary addressing and revaluing of notions of female virtue as defined, among others, by Samuel Richardson in Pamela and Clarissa, while also anticipating later portrayals of femininity in, for instance, Jane Austen’s works. The Vicar of Wakefield thus not only presents its reader with a complex pattern of eighteenth-century femininity, but also provides insights into contemporary debates on marriage, morality, and women’s agency.