The article approaches the educational potential of aesthetics and the arts by reviving the notion of Bildung and suggesting an interpretation that emphasizes both its social character and the role of artworks and other aesthetic expressions. Bildung is a dialogic process where human relationships are crucial both for the exchange and the birth of insights. Artworks are described as images (Bilde), which act as intermediaries and points of reference in expressing, communicating and negotiating cultural values. In developing the argument, Immanuel Kant’s analysis of aesthetic judgment is read together with his ideas on enlightenment, highlighting the social and political character of judgment. Wilhelm von Humboldt’s discussion of the aesthetic and social dimensions of Bildung provides another starting point. Two examples of contemporary artistic processes are used to indicate the educational and political relevance of art in our time.