This article takes as a starting point the career of Sir Alec Clegg, Chief Education Officer for the West Riding of Yorkshire (1945-1974), and traces his professional connections with educationists in Australia and New Zealand. In exploring the nature of global exchanges between educators, artists, architects and designers in the decades immediately before and after the Second World War, the intertwining of modernism and progressivism is critically explored in the wider contextual frame of the Arts and Crafts Movement. The notion of increasing the humanity of the classroom occupied the efforts of a constellation of individuals caught up in the desire to redesign schooling in ways that would regenerate democratic relations of living in the post-war world. It is suggested that a common thread connected those concerned to strengthen democracy through combining progressive and modernist attitudes with the potent legacy of the Arts and Crafts Movement.