The professional self-images of principals are integrally related to how they perceive and exercise leadership in specific school settings. This study of a balanced sample of male and female leaders from a cross-section of Victorian schools in the late 1990s reveals that there are key variations related to sectorial identity, level and scale of school, institutional histories and even student gender. It supports the development of nuanced theories about leadership and gender that combat essentialist stereotypes which have dominated in past discourse. It also combats simplistic claims based on school level, sector and student gender. The findings carry implications for principal selection and development which require fine-grained discernment by practitioners and theorists in the future.