Architects and designers communicate their ideas within a range of representational methods. No single instance of these methods, either in the form of orthographic projections or perspectival representation, can address all questions regarding the design, but as a whole, they demonstrate a comprehensive range of information about the building or object they intend to represent. This explicates an inevitable degree of deficiency in representation, regardless of its type. In addition, perspective-based optical illusions manipulate our spatial perception by deliberately misrepresenting the reality. In this regard, they are not new concepts to architectural representation. As a consequence, Optically Illusive Architecture (OIA) is proposed, not as a solution to fill the gap between the representing and represented spaces, but as a design paradigm whose concept derives from and accounts for this gap. By OIA we aim to cast light to an undeniable role of viewpoints in designing architectural spaces. The idea is to establish a methodology in a way that the deficiency of current representational techniques—manifested as specific thread of optical illusions—flourishes into thoughtful results embodied as actual architectural spaces. Within our design paradigm, we define a framework to be able to effectively analyze its precedents, generate new space, and evaluate their efficiencies. Moreover, the framework raises a hierarchical set of questions to differentiate OIA from a visual gimmick. Furthermore, we study two OIA-driven environments, by conducting empirical studies using Virtual Reality (VR). These studies bear essential information, in terms of design performance, and the public’s ability to engage and interact with an OIA space, prior to the actual fabrication of the structures.