The Czech surrealist artist Toyen’s work and self-styling cut across gender boundaries. Toyen avoided revealing information about herself, and it became clear that she and her friends collaborated—consciously or not—in the creation of a mythically obscure biography. While the biographies of many other surrealists are well known, Toyen’s personal reticence has rendered her unusually mysterious. In examining the construction of her biography and attempting to place her within an historical context that remains largely unfamiliar to western audiences, this article illuminates how one early twentieth-century female creative figure negotiated male-dominated avant-garde circles and how in some cases female cultural workers were marginalized less by their peers than by the cultural establishment or historical circumstances. This very private artist provides a unique and exciting opportunity to study one woman’s role in three important avant-garde groups (Devětsil and the Prague and Paris surrealist groups) and negotiation of nonconformist gender roles and the erotic.