Sustainable urbanism offers a set of best practice planning and design prescriptions intended to reverse the negative environmental consequences of urban sprawl, which dominates new urban development in the United States. Master planned developments implementing sustainable urbanism are proliferating globally, garnering accolades within the planning community and skepticism among social scientists. Despite attention from supporters and critics alike, little is known about the actual environmental performance of sustainable urbanism. This dissertation addresses the reasons for this paucity of evidence and the capacity of sustainable urbanism to deliver the espoused environmental outcomes through alternative urban design and the conventional master planning framework for development through three manuscripts. The first manuscript considers the reasons why geography, which would appear to be a natural empirical home for research on sustainable urbanism, has yet to accumulate evidence that links design alternatives to environmental outcomes or to explain the social processes that mediate those outcomes. It argues that geography has failed to develop a coherent subfield based on nature-city interactions and suggests interdisciplinary bridging concepts to invigorate greater interaction between the urban and nature-society geographic subfields. The subsequent chapters deploy these bridging concepts to empirically examine case-studies in sustainable urbanism. The second manuscript utilizes fine scale spatial data to quantify differences in ecosystem services delivery across three urban designs in two phases of Civano, a sustainable urbanism planned development in Tucson, Arizona, and an adjacent, typical suburban development comparison community. The third manuscript considers the extent to which conventional master planning processes are fundamentally at odds with urban environmental sustainability through interviews with stakeholders involved in three planned developments: Civano (Tucson, Arizona), Mueller (Austin, Texas), and Prairie Crossing (Grayslake, Illinois). Findings from the three manuscripts reveal deep challenges in conceptualizing an empirical area of inquiry on sustainable urbanism, measuring the outcomes of urban design alternatives, and innovating planning practice within the constraints of existing institutions that facilitate conventional development. Despite these challenges, synthesizing the insights of geography and cognate fields holds promise in building an empirical body of knowledge that complements pioneering efforts of planners to innovate urban planning practice through the sustainable urbanism alternative.