From 1957 to 1966, UNESCO engaged in a decade-long project aimed at improving cultural relations, a project that generated transnational discourse over representations of East and West. The international climate of this period was characterized not only by decolonization and Cold War tensions but also by activism that amplified diverse and increasingly strong Asian and Arab voices in intergovernmental fora. Composing nearly half of UNESCO's membership by the mid 1950s, these states' demands for greater agency in the international sphere garnered considerable attention following the Bandung Conference (1955), which rekindled longstanding fears of imminent if not perpetual East-West conflict and also precipitated the call for UNESCO to facilitate interchange around Eastern and Western cultural values. By examining UNESCO textbook exchanges, this article illustrates the regionally distinct representations of Asia and Europe that emerged in the postcolonial context. It reflects regional sensitivities as well as cooperative and sometimes startlingly optimistic positions, which are viewed from a perspective that prioritizes cultural relations as a distinctive framework of transnational analysis informed yet not determined by Cold War paradigms. Through this exploration of intergovernmental efforts to engage states in dialogue on cultural identities in the midst of redefinition and rising ambiguity about the meaning of East and West, this work contributes to a growing body of research on international cultural relations in the 1950s and 1960s.