The twenty-first century brings to our clinical doorsteps increasing numbers of children exploring and questioning their gender identities and expressions. This paper begins with a reassessment of the psychoanalytic thinking about gender and then outlines a clinical and developmental model of gender adapted from D. W. Winnicott's concepts of true self, false self, and individual creativity. The underlying premise is that gender nonconformity, when the core psychological issue, is not a sign of pathology but rather a reflection of healthy variations on gender possibilities. Working from that premise, composite clinical material from the author's practice as a psychoanalytic gender specialist is presented of a gender-nonconforming child transitioning from female to male, to demonstrate the psychoanalytic tools applied, including listening, mirroring, play, and interpretation, with the goal of facilitating a child's authentic gender self. Emphasis is placed on learning from the patient, working collaboratively with the family and social environments, and remaining suspended in a state of ambiguity and not-knowing as the child explores and solidifies a True Gender Self.