Perceptual similarity is one of the most fiercely debated topics in the philosophy and psychology of perception. The documented history of the issue spans all the way from Plato – who regarded similarity as a key factor for human perceptual experience and cognition – through to contemporary psychologists – who have tried to determine whether, and if so, how similarity relationships can be established between stimuli both within and across the senses. Recent research on cross-sensory associations, otherwise known as crossmodal correspondences – that is, the existence of observable consensual associations, or mappings, between stimuli across different senses – represents an especially interesting field in which to study perceptual similarity. In fact, most accounts of crossmodal association that have been put forward in the literature to date evoke perceptual similarity as a key explanatory factor mediating the underlying association. At the same time, however, these various accounts raise several important theoretical questions concerning the very nature of similarity, with, for example, the sensory, affective, or cognitive underpinnings of similarity judgements remaining unclear. We attempt to shed light on these questions by examining the various accounts of crossmodal associations that have been put forward in the literature. Our suggestion is that perceptual similarity varies from being phenomenologically-based to conceptually-based. In particular, we propose that the nature of the associations underlying similarity judgements – whether these associations are phenomenologically-, structurally-, emotionally-, or conceptually-based – may be represented in a two-dimensional space with associative strength on one axis, and cognitive penetrability on the other.