This essay draws on Winnicott's deep insights developed in a series of texts over the last decade of his life and addressing questions of gender and sexuality, as these phenomena shape and are shaped by core experiences in the evolution of intersubjectivity. Interweaving Winnicott's work with that of Loewald, Laplanche and Matte Blanco, the essay speculates about possible developmental processes through which complex and shifting gender identifications intersect and interact with experiences of sexuality and desiring. The essay tracks Winnicott's evolving ideas about gender and madness and opens a way of thinking about one process by which gender may emerge, in a complex, ‘softly assembled’ encounter with desire and being desired. This approach also seeks to reframe and expand the current move in gender theory ‘from etiology to teleology’. The term ‘etiology’ locates us in causation, diagnosis and the sites of pathology, and I think we should continue to be wary of the intrusion of these socially driven biases and ideas into reflections about sexuality and gender in development.