This chapter presents the rise of the avant-garde milieu of designers in Tokyo, which revolutionised visual and material culture beginning in the 1960s and continues to impact it in the present. This milieu included designers such as Ishioka Eiko and Tanaka Ikk? (graphic design), Issey Miyake and Rei Kawakubo (fashion design), Kuramata Shir? and Uchida Shigeru (interior and product design), and And? Tadao and Isuzaki Arata (architecture). These designers all made decisions and created artefacts that radically altered and reshaped the course of Japanese design history. The development of their critical design is presented in the context of the aesthetic, economic, social, and political forces operating during this period and is linked to the rise of critical theories. Moreover, this chapter presents the development of social media and the rich working relations and collaborations among these designers and between them and members of the artistic avant-garde active during these years.