The paper tries to explore the potentialities of a cultural semiotics of images through both a comparison with other semiotic approaches and through the example of a specific analysis: a cultural semiotic study of De Chirico's painting Torino printanière. The traditional Greimasian approach to the semiotic analysis of images, it is argued, fails in explaining how their meaning depends on the cultural contexts of their production and reception. Likewise, the traditional Echian approach underestimates the fact that ideally cooperative spectators are nowadays more an exception that the norm: as a consequence of the globalization and digitalization of images, more and more people lack an adequate “encyclopedia” to interpret images they are confronted with. The paper therefore claims that a cultural semiotics of images is urgently needed, and contends that the school of Moscow/Tartu can provide many suggestions about how to conceive it. According to Jurij M. Lotman's theory, indeed, images must be interpreted in relation to their semiosphere, a hypothesis ― formulated through the meta-discourse of semiotics ― about how a culture produces and manages meaning both inside such culture and in relationships with what such culture considers as external to it. However, the paper points out, in Lotman's theory the semiosphere is not only a repository of texts, but also a mechanism that produces them. As a consequence, semioticians can both study a semiosphere in order to understand the meaning of an image, and analyze an image in order to understand the meaning of a semiosphere. The paper concludes that only the synergic approach between micro-semiotic and macro-semiotic analysis ― including the methods of post-greimasian semiotics ― is able to formulate solid hypotheses not only on what images meant at the moment of their production, but also what they mean when they are received in a completely different semiosphere, by people whose visual culture is sometimes radically different from that of the image's original context.