The Working Pupils’ Association of High Schools was founded in 1960s’ Greece as an organization of working boys and girls who attended secondary evening schools after having finished their daily waged work. Acting simultaneously as a conventional union and as a collective that encouraged artistic activity, the association elaborated new meanings about the relation between work, education, and youth. The postwar period saw the rapid expansion of secondary schooling to the lower classes, which affected deeply both youth and the working class. However, significant attention has not yet been paid to pupils generally, let alone to those of the working class. Addressing this lacuna, this article suggests a new perspective on the relation between the histories of youth, class, political acculturation, and social change in the second half of the twentieth century.