Kevin Lynch’s The Image of the City (1960) is a seminal urban design theory notable for its clear delineation of urban form, empirically rooted methodology, and synthesis of architecture and planning as an important domain. Since its publication in 1960, however, urban experience has evolved alongside the pervasiveness of information and communication technologies (ICTs). Given this new information landscape, we present two research efforts that seek to define the legibility of cities today. The first approach investigates the relevance of Lynch’s five urban elements and the effects of ICTs on environmental perception during wayfinding. Findings show that mental images of cities are shifting in focus to include places of functional signific...