Scholars in critical masculinities studies argue that we need men involved and engaged in gender equity movements for gender justice to be realised. Yet we need to know more about how different groups of men are understanding gender equity and what the barriers might be. Amidst significant media interest in elite private boys' schooling and its possible (re)production of sexist cultures, this paper explores how 13 men who attended such schools in Australia between the 1970s and the 2000s understand gender justice, revealing a diversity of positions and practices across the different generational groups. We argue the men's engagements with gender justice are shaped by a broad 'curriculum of privilege' including school and non-school based experiences that mediates their lives. Further research with both elite boys' schools and their alumni is needed to better understand generational change in their engagements with gender justice.