Over the last decade, education researchers have been concerned with the "impression management" activities of schools in the current climate of school corporatisation. Among these activities is the dissemination of school prospectuses that, far from being merely arbitrary sources of information, are seen as strategic texts that communicate the ethos of educational providers to potential clientele. Through sociocultural, feminist and post-structuralist frames, we consider how the positioning of masculinities is utilised as a marketing technique in such texts and, in turn, how such texts are implicated in the discursive construction of idealised schooling subjectivities. We undertake a semiotic analysis of the prospectuses of six private boys schools in the Sydney region of New South Wales, Australia, considering how masculinities are represented within binaries that position older boys as hard, strong and capable, and younger boys as small, weak and vulnerable. We argue that schooling is depicted in these texts as providing the necessary training ground for boys making the transition from boyhood to manhood. We argue that these images of masculinity continue to be associated, either directly or indirectly, with narrow notions of social privilege.