The paper discusses the aesthetic aspects of place-making practices in the urban environment of Western metropoles that are struggling with the progressive undifferentiation of their space and the weakening of communal and personal bonds. The paper starts by describing the general characteristics of an urban environment as distinct from the traditional vision of a city as a well-structured entity, and in relation to formal and informal aesthetics and participatory design ideas. The author then focuses on two contrary but complementary tactics for translating a space into a positively evaluated place: by domesticating it through introducing nature into an urbanscape; and by accentuating its alienness with the example of the urban exploration movement. The growing popularity of the latter is presented in relation to the discourses related to the decline of cities and the romantic endeavours for reaching into the realm of the unknown or the uncanny in order to rediscover and enrich the unique identity of a place. The paper ends with conclusions that present the necessity for the cultivation of a multidimensional aesthetic awareness and an aesthetic engagement as a crucial issue in the complex task of endowing places with a density of meaning.