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This paper conceptually explores aesthetic labor (AL) as a leadership challenge in affluent school settings, focusing on its implications for teacher wellbeing and inclusive culture. AL refers to how school leaders’ expectations around appearance, demeanor, and dispositions shape teachers’ daily experiences. Drawing on Bourdieu’s theory of habitus, the paper reframes AL as a leadership dynamic in affluent schools where stakeholder pressures reinforce dominant social norms shaping teacher expression of authentic self. The study proposes a qualitative design to explore how implicit or explicit leadership practices may privilege aesthetic norms that marginalize teachers. Despite research on AL’s in other fields, its educational relevance remains under-theorized. This work calls for greater scholarly attention to AL’s impact on inclusion, and teacher wellbeing.