This study investigates the lived experience of one transwoman, Claire, a public advocate and a manager with client services responsibilities. We examine Claire's story in order to discuss how situated contexts, such as different roles, locales and interactions, shape the way she experiences and perceives her trans body and gender identity. In particular, our analysis centres on how Claire's lived experience of personal and professional life shift across three different situated contexts, each enabling and constraining opportunities for political transgression. Our findings contribute to existing conversations within queer theory, transgender and organization studies by highlighting how situated contexts mediate the political potential of queer bodies at work. By developing the concept ‘situated transgressiveness’, this article challenges notions of transgender as a stable, ideal disruptive category and advances a more contextually sensitive approach to understanding the contingency of transgender lives and politics. Such insights are important in facilitating more nuanced understandings of the situatedness of transgression and transgender bodies within work and professional settings.