Otfried Preußler’s and Herbert Lentz’s classic picturebook Die dumme Augustine (Stupid Augustine, 1972) was one of the first German-language picturebooks to focus on a woman’s struggle for professional participation and self-realisation. The book, which has been frequently reissued for over 50 years, deals with questions of gender relations, socialisation, and the distribution of wage labour and reproductive work. Taking Die dumme Augustine as a starting point, this article focuses on the protagonists, discourses, and narratives that revolve around gender, work, and equality in selected Western emancipatory picturebooks from the 1970s and 1980s, especially Anthony Browne’s Piggybook (1986) and the Italian picture book La vera storia dei bonobo con gli occhiali (1976) by Adela Turin and Nella Bosnia. Drawing on perspectives and concepts from feminist theory and approaches from picturebook research, the paper explores how the works address gender discourses of their time and reproduce, negotiate, and/or transform gender images and relationships using multimodal techniques.