This dissertation is concerned with the largely forgotten Munich portraitist Friedrich August von Kaulbach (1850–1920). The focus is on the artist’s numerous portraits of women, which in their entirety offer new insights into the portrayal of female roles and identities in the art world of the German Empire. A systematic review of the extensive legacy in the artist’s villa in Bavaria and the integration of art-historical and socio-historical contextualization provide a comprehensive picture of Kaulbach's work and its significance for the development of portrait painting at the end of the 19th century. This research especially takes the portraits of women by the once celebrated “ladies’ portraitist” into account. These offer an insight into the social standing and expectations of ‘the woman’ at the end of 19th century. A second point of interest is the examination of the hand drawings contained in the artist's estate. Together with Kaulbach's biography, the analysis of the hand drawings and other archival documents provides new insights into the social-cultural context and allows assertions to be made about art production and the role of women in the art world of Kaulbach's time.