This article analyses the historical formation of the specialised retail street Santa Ifigênia (São Paulo, Brazil), and links it with concepts based on an evolutionary framework. Testing of the theory is based on historical data of firms from 1857 to 2010. The research has found that the current specialisation in the electro-electronic sector (from the 1940s onwards) is the third one that has taken place in the street, replacing the previous fashion sector (between the 1910s and the 1940s), which in turn outcompeted the original specialisation of the food sector (from the 1870s to the 1910s). It also highlights the historical and contingent events that changed the trajectories of the retail evolution of the street.