Born in Vienna in 1906 to a wealthy, assimilated Jewish family, the painter Marie-Louise von Motesiczky enjoyed a lively social life among the prominent figures of intellectual and cultural Vienna in the closing years of the Habsburg dynasty. She studied at art schools in Vienna, Paris, and the Netherlands, including with German painter Max Beckmann in Frankfurt. The Nazi rise to power cut short Marie-Louise Motesiczky’s career in Central Europe. She fled Vienna for permanent refuge in England. Like her mentor, Beckmann and her contemporary and fellow émigré artist, Oskar Kokoschka, Motesiczky considered the artistic practice of the self-portrait an occasion for self-questioning, self-affirmation, and self-discovery. Unlike her mentors, from early in her career, Motesiczky’s self-portraits had to negotiate the representation of a female subject. This article will investigate the ways in which Motesiczky’s emigration compelled her to reexamine the gendered parameters of the self-portrait and how that reassessment manifests itself specifically in regard to her engagement with the spectatorial gaze. Her position as an émigré artist will not be analyzed as a burden to be overcome but, rather, as the impetus for reexamining techniques and strategies of female self-portraiture.