This chapter is an historical ‘engagement’ with 19th century city ‘social explorers’, taking in the ‘flânerie’ of Baudelaire and the later idea of Benjamin, Situationism, and walking in the ‘everyday’ with de Certeau, along with the social documentary tradition of text/photography (e.g., the photo book) and street photography. Included here also are the pioneering works on the city and urban experience by the 1920s–30s Chicagoan sociologists (R. E. Park, W. I. Thomas) on marginality, migration, personal and social disorganisation, and formulating life history and ethnographic practices. This discussion (and that in Chapter 1 on mobilities, senses/visual, performative, digital developments in terms of defining the field) will inform Chapter 3, Walking, art-making, and biographical research, on theorising walking, art, and ethnography. It also provides part of the foundation for chapters in Parts II–III, and our Principles and practice: A framework guide to WIBM, at the end of the book, which gives a number of dimensions for practice.