Kenzo Tange’s 1960 Plan for Tokyo and the debates around it betray the architect’s utopian notions in urban design. Such utopianism grew from his faith in the continuing progress of modern technology and its role in the development of society at large. The dramatic socio-cultural changes in postwar Japan stimulated the architect’s techno-utopian ideas, propelling him to pursue a systematic and futuristic approach to urban design that often involved the reorganization of cities on an unprecedented scale. Two important concepts constituted the foundation of Tange’s methodology of urban design: structure and symbol. Elaborated on in several essays, both concepts stemmed from Tange’s understanding of the social meanings of modern technology and both significantly influenced his design approaches. Developed in his early urban projects and theoretical explorations, these concepts were synthesized in the Plan for Tokyo and then blossomed in his subsequent architectural and urban design practice. Therefore it is fundamental to examine what structure and symbol stood for in his theory, and how they informed his urban design. Two projects in the 1960s, the Yamanashi Press and Broadcasting Center in Kofu and the Plan for Reconstruction of Skopje, exemplify Tange’s concepts of structure and symbol respectively, and reveal his approaches to urban design.