Urban spaces and streets have been studied in a variety of ways in Montreal and Paris, but rarely have historians examined the specific relationship between the function of the street and social usage to reflect changes over time. The argument here is for an analytical approach to photographs combined with textual evidence to reveal the urban processes affecting the retail streets of rue Notre-Dame and rue Sainte-Catherine in Montreal, the through street of Boulevard de Sébastopol, and the pedestrian street of rue Mouffetard in Paris. Photographs reflect the success of modern urban transformations to rework the images of the city from various perspectives and for different purposes. They include the bourgeois female shopper on the late nineteenth-century retail and through streets, female retail and office workers interspersed among men on early twentieth-century rue Sainte-Catherine, and the agency of working-class women in the market transactions and peddler trades of rue Mouffetard.