In a context of rapid urbanization and increasingly standardized built environments, urbanism must find new methods of creating appropriate conditions for the variability of contemporary urban life. The city, understood as a system of interconnected processes in constant change, offers a relational way of thinking about urban design. This thesis explores the concept of Relational Urbanism through a strategic design approach that engages the complexity of the site to create variability in the built environment by relating built form to landscape elements. This relational approach has particular potential in post-industrial sites, where challenging existing conditions and processes of remediation resist conventional methods of redevelopment. The thesis focuses on the Toronto Port Lands as a testing ground for this design approach, drawing on the site's industrial heritage to develop a landscape framework and a set of relational rules that will guide the emergence of a diverse urban environment able to change over time. A series of design strategies—remediation parks, urban delta, adapted industry, and differentiated fabric—rethink the challenges of the site as opportunities for public benefit, creating a variegated landscape for built form to respond to. In contrast to a singular static master plan, this method favours multiple flexible strategies that can be deployed incrementally, breaking down the scale of development and allowing it to be realized by a wide variety of stakeholders. Through this approach the thesis seeks to enable the city to intentionally but subtly guide its urban landscape toward diversity and allow its citizens to participate in its continued adaptation