In 1997, Oswald Mathias Ungers, together with Stefan Vieths, published the book, The Dialectic City, which is a commented collection of some of his architectural and urban projects made for Germany between 1991 and 1995. The introduction, a short but remarkable theoretical essay, expresses concern about the loss of identity of the city due to the gradual disappearance of its typical elements, such as the urban block and the urban fabric. This is because of Solitärbau, understood as a jumble of isolated, unrelated buildings. In the opinion of the authors, the dissolution of urban identity started with the Modern Movement’s urban planning and was finally implemented in the contemporary city, or the media-driven city, which is mainly conceived as a net for information sharing rather than a system of public places for social meetings. Consequently, the loss of urban identity coincides with the loss of the millenarian physicality of the city and entails the disintegration of its durable public places, such as streets and squares. In the 1980s, the awareness of this phenomenon gave birth to nostalgic reactions, characterized by neotraditional and anachronistic approaches that the authors rejected. They preferred to recognize the complexity of the contemporary city and to cope with it by means of two strategies, namely, “the city intended as an arrangement of complementary places” and “the layered city.” Almost thirty years after its publication, these two strategies still show architects a possible way to manage urban development without indulging in future-ready, and often inconsistent, concepts. For this reason, even in the present day, they should be analyzed more carefully with respect to the issue of urban identity.