We assume that, in a digitization context, a complete description of the characteristics of any possible kind of Cultural Heritage (CH) entities should necessarily associate with the usual inventory of the standard “physical” features/properties (dimensions, support, style, location, authorship etc.) some information about their most important “semantic” (immaterial, conceptual …) characteristics. In the case, e.g., of the so-called iconographic narratives these semantic features should refer, mainly, to the artwork’s content/meaning, e.g., the behaviors of the represented characters, their reciprocal interactions, the implicit messages to the user/observer associated with the artwork, the connections with other CH entities, etc. We propose then to introduce in the domain of the CH digitization procedures a new “Digital Cultural Heritage Twin” notion, corresponding chiefly to the representation in digital form of the semantic/symbolic aspects of the original Cultural Heritage entities. From a concrete implementation point of view, the creation of these advanced Digital CH Twins entities will necessarily imply the use of complex Knowledge Representation techniques, able to take correctly into account the above semantic, immaterial meanings.