The aim of the chapter is to describe and analyse how the ‘doing’ of masculinity has been performed in Sweden over time, and within two cultural contexts—that of organized (mainly competitive) sport, and physical education in school. Situated within the development of the Swedish welfare state, the research shows that the concept and idea of gender equality is largely a hegemonic sociocultural ideal. At the political and sociocultural level, there is an ongoing movement towards gender-neutral ways of constructing and understanding bodies as well as sport and physical education in Sweden. At the same time the research shows that on an interrelational level, this picture is less clear, as physical education teachers, athletes, coaches and others seemingly tend to talk about gender equality as an ideal, but sometimes fail to practise this in day-to-day living. Nevertheless, embedded in and part of social life at large, the chapter argues that relational patterns are, and will hopefully continue to be, greatly influenced by and part of the Swedish welfare system, which by necessity influences men’s choices in contemporary Sweden concerning how to ‘do’ masculinity and physical activity in relation to more gender inclusive configurations.