The absence of a shared definition of the variable that is sustainability is a volatile element in the multi-factor equation known as ‘the urban landscape’. The sustainable infrastructure of our urbanised habitats is a fundamental matter for planners and architects, but this is often more of a theoretical concern than a practical application of innovative design implementation. The lack of a shared understanding of sustainable practices contributes to a reliance on conventional orthodoxies, and the ‘play it safe’ approach to the design of public spaces structurally and aesthetically. This study focuses on the methodological and creative threads that connect sustainable design concepts to their viable outcomes. The recent phenomenon of significant population growth within UK regional city centres has emphasised the demand for user-friendly ecologically enhanced public spaces. The synthesis of native species ecology and innovative utilisation of hard landscaping is a fundamental element in the establishment of the concepts of ownership and place. The successful employment of these concepts is debatable. The strands that link worthy sustainable architectural and planning design intentions to their seemingly logical conclusions are frayed, tangled and often severed. Through a selection of comparative case studies and examples of advanced initiatives this paper examines the causes of this entanglement and paradoxically also highlights the innovative capacity of reversing the existing ‘fixed mould of aesthetic convention’.