The article analyzes the perception of visual characteristics of the urban environment in terms of cultural values represented in this process. The analysis is based on a sociological study of the cities in the Southern Federal District, conducted by the authors in 2018. Considerable attention is given to the city dwellers’ contradictory attitudes to the city and the factors that bind it with a person. The study attempts to reveal how assessment of the visual urban environment depends on the type of the city. It is shown that the most acute contradictions include the gap between attachment to the city as a “small homeland” and its actual condition (architectural planning solutions, aesthetic appeal, cleanliness in public places, etc.), increased visualization of social inequality, imbalance in the content of monumental propaganda, dissatisfaction with the general cultural level of city dwellers. The study reveals the city dwellers' controversial attitude to the content of advertisements: residents of small cities tend to evaluate them from a more traditionalist standpoint. The practical value of the obtained results is due to the fact that they may contribute to the improvement of visually perceived urban environment and municipal strategic planning.