In the past twelve months, scandals surrounding the behaviour of current and former students of elite all-boys’ schools in Australia have surfaced across the country. A muck-up day list that included a challenge to spit on a homeless person, sexist public chants on a Melbourne tram, and a Snapchat post re-enacting the murder of American man George Floyd, have been part of a larger media salad that has captured the behaviour of boys within these institutions. This individual paper examines the practices and traditions of these institutions and the ways ‘old boys’ reflect on the elite masculinity they were exposed to, and engaged with, while students. Using in-depth interviews and ethnographic fieldwork, I demonstrate how privileged men, aged 25 to 40, navigated the practices, traditions, and expectations of these institutions while at school, and the tension this has generated for them in their adult identities. Through a consideration of performativity, regulation, and rupture, I explore how these men have engaged in processes of simultaneously disavowing and recuperating aspects of elite masculinity. From this perspective, these men are observed to be reproducing and obscuring the privileges of being young, middle-class, white men. By adopting identities that include elements of creativity, independence and sensitivity, these men position themselves as being both aware and supportive of a cultural moment that is pursuing gender equality, social inclusion, and workplace diversity, while also revealing their suitably as advocates and leaders in this environment.