This paper explores the dialectical-rhetorical constitution of stylistic design trends by analyzing a prominent shift in interface design esthetics, from “skeuomorphism” to “Flat Design”. The case study serves to illustrate the continuous negotiation between opposite design positions or “design dialectics” in the debate surrounding the so-called “Flat Design revolution” as well as related historical design arguments. This paper further considers the concerns related to accelerated trend dynamics, particularly in terms of sustainability. Esthetic obsolescence, whereby products are prematurely discarded, is arguably exacerbated by highly persuasive dialectical design rhetorics. In response to this problem, this paper considers the potential of Kenneth Burke’s dialectical-rhetorical approach to criticism, along with his notion of “comic framing”, as a means toward “discounting” polemical design rhetorics.