Walking is fundamental to how we occupy and navigate our world. Our streets are populated by walking, dressed bodies yet the role of walking has been largely overlooked by the field of fashion design. This chapter examines how fashion can play a role in producing experiences and understandings between (dressed) social bodies and urban environments. Firstly, it proposes that walking the city is a critical activity for fashion practice that can be utilised by creative practitioners to build embodied and situated knowledges of place through a methodology of ‘urban flâneurie’. Secondly, it demonstrates how a critically reflective approach to walking can enhance how fashion presentations—such as runways and public events—contribute to place-making through engagement with urban environments. These concepts are explored through a case study of a site-responsive fashion project in Victoria Harbour, Australia, entitled Urban Flâneur, which resulted in two creative public events. Here, walking becomes a method for fashion designers to study complex relationships arising between fashion, culture and place, and to produce outcomes that activate the urban site.