We showcase the urban, social, and technological transformation of Sixth Avenue (La Sexta Avenida) in Guatemala City, by comparing two sets of past and present-day images of the same locations newly taken and from a local photographic archive respectively. We demonstrate the value of historical-pho- to-visual practice by drawing meaning from visual and historical themes and reflective questions. We illustrate an alternative form of knowledge-making in design by developing sets of design principles informed by the meanings drawn. By coupling historical events and knowledge of present-day con- texts, the photographic pairings add another reflective dimension on present and future perspectives of design and pictorial-based research. The photographic pairings diversify our temporal and cultural sensibilities. Historical-photo-visual practice invites designers and researchers to see photographs as social documents and to consider what is revealed when the conventions and practices of past and present are in conversation.