In this paper, we focus on how people perceive the aspect ratio of city squares. Earlier research has focused on distance perception but not so much on the perceived aspect ratio of the surrounding space. Furthermore, those studies have focused on “open” spaces rather than urban areas enclosed by walls, houses and filled with people, cars, etc. In two experiments, we therefore measured, using a direct and an indirect method, the perceived aspect ratio of five city squares in the historic city center of Delft, the Netherlands. We also evaluated whether the perceived aspect ratio of city squares was affected by the position of the observer on the square. In the first experiment, participants were asked to set the aspect ratio of a small rectangle such that it matched the perceived aspect ratio of the city square. In the second experiment, participants were asked to estimate the length and width of the city square separately. In the first experiment, we found that the perceived aspect ratio was in general lower than the physical aspect ratio. However, in the second experiment, we found that the calculated ratios were close to veridical except for the most elongated city square. We conclude therefore that the outcome depends on how the measurements are performed. Furthermore, although indirect measurements are nearly veridical, the perceived aspect ratio is an underestimation of the physical aspect ratio when measured in a direct way. Moreover, the perceived aspect ratio also depends on the location of the observer. These results may be beneficial to the design of large open urban environments, and in particular to rectangular city squares.