Productive analysis of photographically composed urban imagery is a 'wicked' problem due to the presence of multiple, entangled systems. This paper proposes constructive analytic techniques for composite imagery, consisting of digitally generating and superimposing graphic overlaps within and adjacent to original images, producing new images not rationally related to nameable systems. These new images promote pattern identifi cation, which in turn has the potential to inform conclusions about memory and navigation in urban sites. Thus, the diffi culty inherent in systemic urban analysis is shifted to one of abstract image interpretation, and a new set of refl ective strategies becomes relevant. These strategies are illustrated through analysis of two existing systems in a midsize, Midwestern city: a system of pedestrian walkways connecting several downtown buildings, and a system of overhead power distribution structures. The systems have observable characteristics in common. But, while the walkways represent a deliberate attempt to structure memory and thus to aid navigation, the system of power distribution structures makes no such claim. The paper discusses specifi c implications of the method informing the author's ongoing research and architectural design teaching. In conclusion, wider implications are suggested, informing the general question of constructing urban knowledge.