This chapter aims to unearth Namibia’s traditional fashion industry, with reference to the San Khoe Khoe (Nama) and Ovaherero people of Namibia. It focuses on the dress codes of these two tribes across three phases, namely: pre-colonial, colonial, and post-colonial periods. It is further important to reiterate that the history of all community members is always tied to ethnicity and has a significant influence on the fashion industry. Hence, this study’s objectives are twofold: firstly, to explore the historical evolution of the Indigenous Namibian fashion industry, focusing on the fashion choices of the Nama and Ovaherero ethnic tribes across pre-, during, and post-colonial periods. Secondly, to examine the role of cultural fashion in advancing the Namibian fashion industry as a driver of sustainable, economic, and entrepreneurial development. The application of face-to-face interviews and focus group discussions, along with historical documents were used to explore the dynamic tradition and fashion industry among the San/Khoe Khoe and Ovaherero ethnic groups of Namibia. The findings from this study contribute to the body of knowledge, portraying Namibia’s diverse ethnic fashion and historical journey.