Throughout history, urban environments have continually evolved in response to changing patterns of inhabitation, obsolescence, and migration. As political uncertainty and climate change rise worldwide, contemporary planners, architects, and communities are increasingly envisioning a more equitable and sustainable future. Drawing inspiration from various twentieth-century socio-spatial theories, architectural and urban theorist Jane Rendell introduced the concept of critical spatial practice (CSP) as a strategic design methodology. Her framework emphasizes multi-disciplinary approaches to navigate the complexities of socio-spatial dynamics. Rendell employs trans-scalar thinking to see the built environment as a nexus of flows, atmospheres, and narratives. Critical spatial practices, much like the contemporary city, traverse space and time to address development pressures and ecological concerns. This chapter explores an interdisciplinary academic design studio that applied critical spatial practices to study Chinese hutongs and American alleys. These outdoor-indoor street networks foster unique socio-spatial environments that nurture both people and culture. Here, the interplay of alleys and architecture is examined through the contrasting urban morphologies of Beijing and Cincinnati.