This research initiative addresses the issue of Design in relation to Virtual Context. Central to this study are the innovative potentials and instrumental opportunities of computer based media techniques, capable of generating interactive models and changing perspectives for the benefit of urban and architectural design. The ambition was to not only make a contribution to the existing body of knowledge concerning digital technologies and their applications, but explore theoretical conditions which might help define and stimulate further study. From the outset, the focus was on furthering the opportunities for computer based representation media in creative design. On the basis of a series of explorative studies the subject of this research was targeted: the issue of Design in Context, or more specifically: Design(ing) in a Virtual Context. During the process there was a marked shift in the conception of the subject from -more or less immersive- VR technologies in the direction of approaches which might be expected to become readily available in practice and education and could be effective in actual design processes. This insight also brought about a shift in emphasis from realism per-se towards creating a sense of situatedness. The design representation system which was developed was intended to not just allow for one type of model view, but to afford an array of different views, from which the designer would be able to choose freely, depending on the phase and focus of design as well as personal preferences. A series of interface prototypes and support tools were developed especially and successively tested experimentally. For the intended final design driven experimental study, different virtual context models were considered. Eventually, an integral ñ purely fictitious ñ design ëenvironmentí was constructed in the computer, so that the workings of the proposed system and its components would be tested systematically. A conscious choice was made for an in depth study, on a relatively modest scale, which would a certain amount of mutual involvement between designer and researcher, to confront the participants with the finer aspects of the proposed system in a relatively short time and to gather detailed data. A half dozen design professionals were invited to participate in a closely monitored experimental exercise. The results of this study therefore do not offer straightforward, indisputable facts, to be considered representative for the design community as a whole, but indicate that the working methods of the individual designers -when discovering aspects of the site, developing and presenting proposals and reflecting on the qualities of represented designs- tend to vary considerably. For this reason the interactive representation system proved to be of value. Participants could express different view preferences, with more or less realistic image modes being used in different phases of their design developments, with varying experiences of situatedness. Some of the design professionals participants were very appreciative of the systemís opportunities, others tended to be more set in their ways. The results of this experimental study indicate that there may particularly be opportunities for interface applications which are able to function interactively, offering individual designers -as well as others involved in evaluating design proposals- a variety of tools with which to approach specific design artefacts in their changing contexts. Virtual models can play not only an important role as a 'reminder' for the designer but also to other parties playing an active role in the design and implementation processes. Interactive environment models are not only promising as exploration tools for existing sites, but could be valuable to test the impact of a design on its location. This could be especially interesting if the site is difficult or impossible to visit or as yet a virtual construction. In addition such an approach might be beneficial for objective comparison and evaluation of design proposals in competitions and in education as well as in on-line collaborative design projects where the context is still in the process of being developed.