Apart from interactivity, representativeness (in the meaning of grandness) is the basic and required characteristic of public open spaces. The representativeness of public open spaces (POS) is understood in terms of their ability to portray cities and their inhabitants as a whole. This study considers the historical value of public spaces and determines their contemporary role as spaces for representing cities. Moreover, we explore the relationship between the natural value of such places and their representativeness function. It was necessary to define the criteria determining the representativeness of public spaces, including their physical, semiotic, and functional features. The study was carried out in the midtown zone of Szczecin. The subject of the study is urban landscape objects. The landscape, according to the definition presented by the European Landscape Convention, is part of the land, as perceived by local people and visitors, which evolves through time as a result of being acted upon by natural forces and human beings. The landscape approach used in this research enables an assessment that requires taking into account and comparing many aspects that build the layers of the landscape. Qualitative and quantitative research methods were used to assess the characteristics that distinguish POS in the symbolic, formal, location-related and functional layers and to examine their ecological value. The results of the study generally confirmed our hypothesis: i.e., embedding the studied POS within the city’s tradition—with its strong semiotic connections and with the specific history of the place (genius loci)—increases the space’s range of contemporary, representative functions. At the same time, an apparent decrease in the prestige of the studied POS was observed. Although they originally had high historical value, they either lost key artifacts constituting that identity or were excluded from the main functional and compositional axes of the city. Moreover, this study proves that the representativeness of POS, conditioned by historical value and contemporary functional, spatial, and location features, is generally inconsistent with their high natural value. Still, this inconsistency does not have to be a mean contradiction.