Through examples such as the Haas Haus in Vienna and the Sainsbury Wing of the National Gallery in London, this text examines the shifting appreciation of architectural eras and Postmodernism. Beyond decorative Post-modernism and the focus on form, the movement’s broader facets are explored—including participation (Ottokar Uhl, Eilfried Huth), ecology (Friedensreich Hundertwasser), grassroots movements (the 1976 “Arena” occupation), and sensitive urban renewal, along with their lasting impact on Vienna. These crucial directions of Postmodernism are often overlooked in contemporary criticism and evaluation. The use of irony as a stylistic device is illustrated by Hans Hollein’s design of Vienna’s Michaelerplatz. Furthermore, the Vienna Oktoneum (1986) by architect Peter Czernin—a Postmodern office building in the 3rd District—has been listed as a protected monument since 2024 as a “Gesamtkunstwerk” (a total work of art). The initial criticism of this building and the successful mediation work that led to its reappraisal are also explained.