The contemporary large-scale megalopolis is complex, full of inconsistencies, economic oscillations, mixed-hybrid forms, and ever-changing environmental consequences. If our urban territory embodies imbalanced heterogeneity, how can we confidently design resolutions to offer such flexible results? Borrowing models found in mathematics, topology – a configuration of point sets or properties remaining invariant through transformational states – might offer clues for continuous states of urban metamorphosis. Observing the horizontal urban domain topologically elastic, conformed to a sub-set of limits, can activate design decisions within such inconsistent circumstances. Using a series of case study sites in one of the largest cities in the world, Shanghai postulates an urban setting packed with paradoxes of continuously broken behaviors. In the realm of contemporary landscape urbanism practices, this paper suggests methods of combining topological space and topographic extensivity for modeling and designing the future city.