This article focuses on ways of building preservice primary teachers' confidence in teaching art with artworks and, in particular, on how to develop their pedagogical content knowing. It is suggested that through opportunities offered for engaging in observational and reflective practices with artworks an initial groundwork is set that can challenge pre-service teachers' preconceptions about art and promote an aesthetic form of inquiry. A qualitative approach was followed which included in-depth interviews with twenty pre-service teachers regarding their attitudes and knowledge towards artworks. The findings indicate that enhancing teachers' abilities to practice factual inquiries and then move on to interpretive inquiries of artworks can help them learn how to learn about artworks and how to organise meaningful art viewing activities with children. Issues relating to the participants' level of aesthetic understanding are also discussed as participants were asked to engage with artworks and their aesthetic encounters were documented.