Using multi-faceted case studies, the author presents the early modern aesthetic discourse in Lombardy. It analyzes the relationship between theory and practice and discusses historical media reflections as well as questions of knowledge. From the perspective of art history, literary studies and the history of knowledge, Mira Becker-Sawatzky analyzes visual art practice and textual theory in their partly dialogical, partly discrepant relationship to one another. For this purpose, painting, drawing, sculpture, poetry and tractistics, each with their specific mediality and materiality, are set in relation to one another in thematic clusters. The reordering of the hierarchy of knowledge, the plurality of the Paragone, the virulence of grotesque aesthetics, the conception of artistic styles, the dimensions of meaning of vaghezza and the roots of the Ambrosiana in Milan are examined.