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Women's bodies are abject and ‘out of place’ in organisations where (self and other) disciplining of women's bodies serve to regulate and silence women. Yet we know little about how expectations of body and appearance play out in the career decisions and everyday practices of women academic leaders. In this chapter reflexive accounts are used to explore if dress and appearance expectations have implications for women's career development and advancement, specifically in the context of business schools. The literature review and two reflexive autoethnographic accounts provided, illuminate how, through dress and appearance, the pervasiveness of hegemonic masculinity is both sustained and challenged and the potential impacts of this upon women's careers in academia.