This article explores the relationship between colonial ideologies and urban planning in the context of the pre-war Japanese empire. It does so by examining the second largest city in what was Japan's first formal overseas colony of Taiwan. By exploring some of the key texts through which the city of Takao (Kaohsiung) was depicted and its future debated in the colonial era, the ways in which imperial ideologies, such as the ‘southern advance’ of the Japanese empire, influenced and were reflected in urban space will be considered.