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The economic geography of cities is often thought to have changed dramatically between the medieval and early modern eras. The medieval city is seen as having been strictly regulated, both in terms of markets, and in terms of space. The early modern city, by contrast, is associated not only with growth, but with the breakdown of rigid regulation by guilds and a new commercial outlook. However, empirical studies of the spatial organization of medieval cities have been limited, and quantitative surveys of urban economic geography have focused on the seventeenth century and later. This article analyses the spatial distribution of occupations in the City of London between the 1370s and the 1550s using a large probate dataset. It examines occupations that remained clustered or dispersed, but concentrates on the apparent breakdown in economic clustering among London’s leading trades. Prosopographical analysis reveals that merchants and retailers became more specialized, but that this was accommodated within London’s existing guild-based occupational identities, which had become ossified. Rather than the end of the middle ages having marked a dramatic change from guild-based spatial organisation, occupational clusters simply continued to evolve in line with the principles of locational economics throughout the period.