This chapter explores the transformation of metropolitan Tokyo through the examples of its vernacular urban alleyways, the roji, and argued to approach changing urban forms through their spatial, social and cultural dimension and through the nuances and sequences that unfold between the marginalisation, re-appropriation and re-invention processes. The alleyways, which are the urban fabric, everyday place and lifeline of people coming from all walks of life, foster the “mingling of diversity” and “knowledge spillovers” as Jane Jacob described it. The task for the new generation is it to continue to find ways to preserve the area and alleyways in an active way without creating a museum-like neighbourhood. Multiple and hybrid identities, as observed in the case of Tsukuda and Tsukishima, co-exist in the same place, and it depends on the perspective of the user as to how an ordinary place like the alleyway is perceived and valued.