When studying Kowloon Walled City, existing scholarship evaluates its political, architectural, and social aspects separately. This paper aims to synthesize these three aspects and provide a comprehensive understanding to Kowloon Walled City, by examining the impact of British colonial history on the transformation of architecture and living conditions within Kowloon Walled City. It begins with an investigation into the causes that led to the anarchic status of Kowloon Walled City in the 1960s, followed by an evaluation of the architectural transformation with reference to the Building Ordinance 1950 edition. Through a synthesis of historical review and analysis of visual records, this paper validates that the anarchy status attributed to the British colonial history had the major impact on the deterioration of underprivileged living conditions in Kowloon Walled City.