The present study, part of an in progress complex research, aims to investigate the understanding of urban architecture and the preference of the citizens with respect to different architectural styles. This first exploratory study, starting from an interdisciplinary viewpoint, is focused on deepening the diverse perspective of urban psychologists and architects in order to realize communicative procedures of urban planning towards a social sustainable design. The theoretical background of the study is related on the role of architecture in human-environment transitions (Bonnes et al. 1990; Garcìa Mira et al., 2005; van der Voordt , 2005; Thompson, 2005 among the others) and, particularly, in the model of participated design (Sanoff, 2000, 2001). On the perspective of Environmental Urban Psychology (Bonnes, et al. 1990; Nenci, 2003), starting from the hypothesis that varying urban architectural typologies affects inhabitants' social life, architects and urban psychologists investigated: a) the evaluation given by urbanites upon the buildings of their city in relation to the understanding of the history of architecture; b) inhabitants' residential satisfaction in relation to other prototypical cities. Via a dialogue conducted by urban psychologists, the following study integrates householders' ingenuous point of view with the expertise of the designers. The study involved a sample of 120 subjects, balanced by sex and age. The subjects performed a self reported questionnaire to investigate: a) their level of appreciation for architectural typologies (contemporary, contemporary relating to the historic, and historic) b) the understanding of key elements of the history of architecture, c) their preference for other prototypical cities (ancient, modern, big and small). Architectural types and prototypical cities had been selected by expert architects. The results seem to show an influence of the architectural typology on urban preferences. In particular, people evaluate more negative contemporary buildings than ancient ones. A sparse understanding of the story of architecture has been detected. Furthermore, results did not show a direct correlation between preference for ancient buildings and the desire to live in ancient cities. Theoretical and methodological implications will be discussed.