This thesis seeks to analyse the notions of historical and physical authenticity as applied to the contemporary cityscape. I propose that criteria of authenticity can be established through study of social interaction within the cityscape. Authenticity reveals itself as the spatial reflection of the lived experience of the city's inhabitants. Following the liberalization of politics and the media in 1987, Taiwan has become a maze of competing and conflicting ideologies and visual images. The cityscape of Taipei reflects this political and social change, making it difficult to distinguish between the authentic substructure and simulacrum. In such a complex environment, people cling to the concept of authenticity in order to retain their sense of identity. Taipei has therefore been chosen to examine how such historical, economic, social, political, and cultural factors impact on the transformation of urban environment. Shopping streets provide the best illustration of the conflict and negotiation between global and local culture in contemporary cities. They stimulate and witness a dialogue between historicism and capitalism. Asian cities, such as Singapore, Hong Kong and Taipei, express the adoption of Western market economies and the trend toward political liberalisation and democratisation in their modern architecture and lifestyle. Their cityscapes have undergone drastic urbanisation and become non-places, as a characterless and universal commercial culture has dominated the production of urban space. Their streetscapes, however, apparently so "inauthentic", are actually the genuine result of contemporary economic, social and cultural forces. The framework of my analysis is grounded on ideas and definitions of social space derived from the work of Henri Lefebvre and Edward W. Soja. Four particular areas are explored to establish a definition of authenticity: the history of development, the memory of place, visual simulation, and mobility within space. This framework is then applied to two representative streets, the historical Ti-Hua Street and the modern Chung-Hsiao East Road in order to investigate how the social, political, and economic changes that have resulted from the process of Westernisation are reflected in the spatial structure of these commercial streets. Through the application of this framework, the condition of authenticity is questioned and identified in the city.