This article explores the development of Medellin city (Colombia) urban commerce of fashion at the first half of 20th century, analyzing the configuration of its geography of fashion. In doing so, the article plots a cartography of city places and spaces transformed by Medellin human masquerade into emblematic settings for the performance and fashion consumption. In a chronological order, the article unveils a shopping map starting at Berrío square, follows to Colombia St. ending on Junín Av. Argues that despite the historical importance of Berrío square and Colombia St. in configuring a territory for experimenting fashion as a commercial practice and cultural, Junín Av. occupies the popular imagination as the first fashionable promenade in Medellin, therefore, addresses to the role of former both places in the configuration of Medellin's fashion geography, in the context of a town undergoing a transformation: going from being a small village to a modern city.