In the first part of this article, I examine new concepts of masculinity and the implications of these concepts for the practice of school administration. I also discuss the "gender subtext" of school organizations as one of the mechanisms through which masculinity is enacted and masculine stereotypes are reinforced within the school setting. In the second half of the article, I offer a vision of gender in schools that seeks to make the full range of gender expression available to all organizational members. I also describe several strategies that could be used by educational leaders committed to gender equity and the cause of social justice. Finally, I assert that there is a need to alter the socialization and preparation of school administrators for these changes to occur.