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The built forms of New York City and Boston differed dramatically in the second half of the nineteenth century. This paper focuses on the changing forms of their retail districts and evaluates the divergence in those patterns in relation to their socioeconomic context. Historical atlases and city directories identified the locations of department stores, which were used as indicators of the retail districts while primary and secondary historical sources related locational decisions to their economic position and the structure of their elite classes. New York's unstable elite classes continued to move their residences north on Manhattan Island throughout the latter half of the nineteenth century and were unable and unwilling to stop the northward expansion of the retail district. Boston's stable ruling class was able to control retail expansion through various political acts limiting development and through social barriers that limited displays of conspicuous consumption. The importance of the structure of elite classes in mediating the processes of land allocation suggests that findings of New York, as a city of competitive capitalism with a splintered elite, and Boston, as a city of controlled capitalism with a ruling elite, might provide a useful framework for understanding the specific contexts within other urban built forms.