Design is an operational concern, dealing with various layers of information to solve a particular problem. When the urban design is the preferred scope, so-called design problems must be transmuted to society’s demands. Accordingly, urban design is a complex problem-solving task that could easily be endangered by oversimplification or chaos. As Kipnis put “heterogeneous space as a democratic space, is different from homogeneous universal space of modernism and incongruous heterogeneity produced by postmodernism collage.” As an urban showcase for “democratic space,” this research attempts to decode the spatial organization of the most resilient urban structure in Iranian cities, Isfahan Bazaar. Bazaar, in general, and Isfahan bazaar, in particular, is an urban phenomenon with an interwoven network of social, political, and cultural factors, representing remarkable adaptability and mutual relation to city transformation. A bazaar is a subtle urban-historical development with respect to demands, environmental forces, and transformations that have taken place in the social, cultural, and political context of the society. The idea of historical development is consistent with self-organization and evolution in biology proposed by Niklas Luhmann in the context of the development of society in general and its sub-systems in particular. This idea was not well flourished in the context of urban topologies.