This paper aims to theorise how virtual reality (VR) can contribute to the development of contextual architecture. We start by considering how an architectural context may translate into a virtual domain, introducing preliminary definitions of what a virtual design context (VDC) could entail. We then discuss a proposed taxonomy that guides the creation of such a VDC, anchored in principles drawn from virtual realism in art philosophy and contextualism within architecture. This taxonomy is envisioned as a preliminary framework for developing VR-driven design environments with a focus on context. Next, we conducted expert user-testing with 24 architects using two VDCs developed according to the taxonomy. The goal of this step was to gain insights regarding the cognitive load of designers and their user experience while engaged in different types of VDCs. Results suggest that designing in these virtual environments enhanced contextual learning, supported conceptual and creative insight and helped maintain manageable cognitive load. The paper concludes by underscoring the real-world applicability of this taxonomy, highlighting how VR can breathe new life into contextual design, not by reducing context into a digital replica, but by opening new dimensions through which its richness can be explored, interpreted and reimagined.