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This dissertation examines how transgender feelings and gender variation emerged as a vital motivator for scientific and aesthetic explorations of human personhood and social experiences of marginality in German-speaking culture in the early twentieth century. My research illustrates how concepts of gender variation served as a generative problem for modernist practitioners of sexual science and as a creative impulse and figural resource for modernist literary and artistic innovations. The feedback between these fields allowed for novel social categories to develop in a period where designations like “transgender” or “transsexual” were not yet in use as stable public identities or diagnoses, but nevertheless circulated in response to experiences of embodied difference and social alienation. By reading for “transgender feeling” as a heuristic that unites multiple historical categories of gender and sexual variation, I argue that transgender phenomena were instrumental for the development of German modernist movements at large. Building on affect studies, trans and queer studies, and German literary and cultural studies, my project intervenes in limited contemporary understandings of transgender history and identity as a minority political and diagnostic discourse. Instead, I argue for a more expansive, “democratized” notion of transgender feeling that encompasses diverse historical forms of gender variation, some of which have disappeared or become “obsolete,” and show how narratives of gender intermediacy and incongruence are essential to modernist aesthetic practices. Chapter One examines theories of sexual intermediacy in the sexological work of Magnus Hirschfeld and Otto Weininger, who both suggested that a transgender condition underlies “normal” human sexual development. I show that trans feelings cut across Hirschfeld’s sexological categories and, in particular, his deployment of the case genre, troubling stable taxonomies of sexual affect and allowing for promising forms of coauthorship and “trans genre writing” to emerge in sexology. Chapter Two takes up Rainer Maria Rilke’s writing in The Notebooks of Malte Laurids Brigge and Das Stunden-Buch, as well as his early childhood experience, to argue that dysphoria and intermediacy are key to understanding the social alienation that Rilke expressed in his modernist work alongside personal attachments to femininity and a feminine poetic voice. Chapter Three on Else Lasker-Schüler illustrates how trans feelings, the masculine persona of Jussuf and appropriations of racial and ethnic difference significantly frame the novel Mein Herz and become enduring features of Lasker-Schüler’s literary and artistic production. I highlight how scholarly reception of Rilke and Lasker-Schüler’s work have intentionally disavowed these expressions as transgender and argue for a reassessment of trans feeling as a creative impulse in German modernism through their texts and images. My last chapter explores how modernist periodical media served as a vital tool for crafting trans intimate publics in the Weimar period and for negotiating the shared norms of gender and social participation for a novel class of gender-variant people under the category of transvestism. In my conclusion, I turn to the unfinished business of sexual and gender definition that continues to frame LGBTQ politics in Germany and abroad today, and I link contemporary questions of trans aesthetics to modernist dynamics of gender and sexual multiplicity.