This article seeks to facilitate an understanding of how boys construct their masculinity in a school environment. More specifically, Franco-Manitoban boys from grades 11 and 12 were interviewed in order to better understand this phenomenon through their participation in social groups and communities of practice at school. Boys negotiate and display multiple versions of masculinity in diverse social circumstances. Each social context has a significant impact on constructing masculinity that in turn affects boys’ lives in school. This thesis is qualitative in nature and uses an ethnographic “lens”. Connell’s (1987; 1995; 2002) social theory of gender with a particular look at hegemonic masculinity, as well as Wenger’s (2005) social theory of communities of practice, were used to analyse data. Results indicate that the masculinity in this particular school environment seems to be based on a traditional model, which includes an adherence to a hegemonic masculinity. Furthermore, the image that relates to the ideal masculinity does not allow boys to consider other forms thereof.