In this paper we adopt the approach that designing is a series of situated acts, ie designing cannot be pre-planned to completion. This is based on ideas from situated cognition theory that claims that what people perceive, how they conceive and what they do develop together and are adapted to the environment. For a system to be useful for human designers it must have the ability to associate what is learned to its environment. In order for a system to do that such a system must be able to acquire knowledge of the environment that a design constructs. Therefore, acknowledging the notion of situatedness is of importance to provide a system with such capability and add on a new dimension to existing learning systems in design. We will call such a learning system within the design domain a Situated Learning Design System (SLDS). A SLDS should be able to create its own situational categories from its perceptual experiences and modify them if encountered again to link the learned knowledge to its corresponding situation. We have chosen architectural shapes as the vehicle to demonstrate our ideas and used multiple representations to build a platform for a SLDS to learn from. In this paper the notion of situatedness and its role in both designing and learning is discussed. The overall architecture of a SLDS is introduced and how the potential outcome of such a system will support human designers while designing is discussed