This chapter examines the historical emergence and evolution of urban economic informality in general and in the African continent as well as South African and Zimbabwean cities in particular. Parts of Africa with a long history of precolonial urban development, such as West Africa had entrenched urban economic informality which survived colonial conquest. However, the same cannot be said about much of South Africa and Zimbabwean cities, which grew after and as a result of colonial conquest. The consequent colonial and apartheid planning laws meant that it was easy to disrupt and tame urban economic informality during the colonial period. In post-apartheid South Africa and post-independence Zimbabwe, the growth of urban economic informality suggests the interplay of a complex myriad of factors and processes deeply embedded in the political economy of these nation states in an enduring way. These observations unsettle some of the enduring assumptions around the development and characteristics of urban informality in the cities under consideration.