Comfort as a technical term in the domain of architecture has been used meticulously to describe, assess, and understand some of the essential qualities of buildings, across four dimensions: visual, thermal, acoustic, and respiratory. This body of knowledge can be drawn upon to shed light on the growing branch of HCI that pursues a shift from “artifact” to “environment” (and from “usability” to “comfort”). We contribute to this conceptual-contextual transition in three consecutive steps: (1) sketch the outline of comfort studies in the scholar field of Architecture and the ones in Human-Computer Interaction, (2) propose a schematic model of comfort that captures its interactive characteristics and, (3) demonstrate an interactive tool, called ComfortBox, that we prototyped to help answer some of the research questions about the perception of comfort in built environments.