This book critically examines the philosophy of the term ‘transgression’ and how it shapes the utopian vision of contemporary urban design scenarios. The aim of this book is to provide scholarly yet accessible graphic novel illustrations to inform narratives of urban manifestos. Through four select case studies from the UK, Cyprus and Germany, the book highlights the paradoxes and contradictions in architecture and provides detailed evaluation of the limits and contemporary forms of sustainable urban regeneration. The book proposes an ‘utopian urban vision’ approach to social, political and cultural relations, trends and tensions – both locally and globally – and seeks to inspire an awakening in architectural discourse. The book argues that the philosophical undermining of transgression is the result of a phenomenon from a different perspective – its philosophical background, social construction, experimental research process and design implications on the city. As such, the book provides a critical examination of how architectural design interventions contribute to sustainable urban regeneration and gentrification and can impact local communities. This book provides a significant contribution to both undergraduate and postgraduate students, as well as early career researchers working in architecture, planning and sustainable urban design. It offers effective guidance on adopting the state-of-the-art graphical illustrations into their own design projects, while considering contradictions between architectural discourse and the philosophy of transgression.