This chapter explores the perception and modeling of style in design relating to visuo-spatial representation and reasoning. We approach this subject via cognitive and contextual considerations significant to the role of style during designing. A designer's ability to represent and reason about design artifacts visually and spatially allows meaningful "chunks' of design information to be utilized relative to the designer's task and context. Central to cognitive and contextual notions of style are two issues, namely the level of semantic interpretation, and the comparative method's degree of contextual sensitivity. This compound problem requires some explicit and cognitively plausible ordering principle and adaptive measure capable of allowing for dependencies in reasoning about similarities. This chapter first investigates the perception of style in relation to these modeling requirements before demonstrating and testing their implementation. We then discuss style in relation to design tasks and how they can be supported via the classification and retrieval of designs from large databases of visuo-spatial information.