In recent decades, research on gender incongruence has shifted from a pathologizing perspective to a more complex approach, research on gender incongruence has shifted from a pathologizing perspective to a more complex approach that recognizes the diversity of gender identities and experiences. This paradigm shift, exemplified by the removal of Gender Incongruence from psychiatric disorders in ICD-11, has impacted psychoanalytic theory and clinical practice, which have traditionally been rooted in etiopathological and reparative perspectives. Psychoanalysis now focuses on understanding transgender and gender diverse experiences, emphasizing individuals’ subjectivity and addressing the challenges this people face in their developmental trajectories, including gender dysphoria and environmental responses to their gender incongruence, by adopting an “affirmative approach” to gender experience. This manuscript first traces the transformation of the scientific approach to transgenderism in contemporary medical-psychiatric discourse, highlighting the shift from pathologization to recognition of the normative nature of gender diversity that has been driven by political, social, and cultural movements. In a second section, the manuscript examines the evolution of psychoanalytic thinking about transgenderism, beginning with classical perspectives and ending with recent contributions, recognizing that much in the field is still evolving.