This article focuses on the continuing impact of recuperative masculinity politics in the schooling of economically advantaged boys (elite and middle class); yet, it also indicates resistance to this politics. An understanding that the gender order is unstable and that variants of hegemonic masculinity continue to morph in the context of globalisation is also exemplified. Two case studies are analysed, both focused on remaking masculinities: Balfour, an elite all boys' school in Scotland and Springtown Religious School, a middle-class, coeducational Australian school. The cases show that the remaking of masculinities is shaped by social class politics and confirm the diversities within the categories of "boys". At Balfour, the remaking of elite masculinities was framed by the perceived needs of the globalised labour market (especially in finance) and the changing practices of professional, elite femininities. At Springtown, a school known for rejecting competitive sport and for their commitment to gender equity, girls and some staff resisted changes to the outdoor education programme framed by recuperative mythopoetic discourses. The article illustrates the production and reproduction of privilege and advantage and the remaking of elite and middle-class masculinities within an ever-changing gender order, an important insight for those working towards socially just gender policy and praxis. (Contains 3 notes.)