The aim of this position paper is to establish an initial approach to the automatic classification of digital images about the Outsider Art style of painting. Specifically, we explore whether is it possible to classify non-traditional artistic styles by using the same features that are used for classifying traditional styles? Our research question is motivated by two facts. First, art historians state that non-traditional styles are influenced by factors “outside” of the world of art. Second, some studies have shown that several artistic styles confound certain classification techniques. Following current approaches to style prediction, this paper utilises Deep Learning methods to encode image features. Our preliminary experiments have provided motivation to think that, as is the case with traditional styles, Outsider Art can be computationally modelled with objective means by using training datasets and CNN models. Nevertheless, our results are not conclusive due to the lack of a large available dataset on Outsider Art. Therefore, at the end of the paper, we have mapped future lines of action, which include the compilation of a large dataset of Outsider Art images and the creation of an ontology of Outsider Art.