This article presents findings from a creative qualitative study, where drawing was used as a methodological tool to investigate university students' awareness of homelessness. Previous research (Breeze and Dean 2012; 2013) has shown that homelessness charities often utilise stereotypical images in their fundraising campaigns, focusing on the arresting issue of rough sleeping (rooflessness) as opposed to other, more widespread experiences of homelessness. In drawing 'what homelessness looks like' the images students produce are often rooted in familiar local scenes - local roofless people they see regularly, or replications of common media images, with a tendency to depoliticise and individualise homelessness as a social issue. These drawings show striking similarities, common themes, and indicate a lack of critical engagement with the complex problems within personal homelessness narratives. The efficacy of the methodological approach is assessed, with the role creative methods such as drawing can play in stimulating critical discussion of issues, such as gender and the media, highlighted. The article also argues that such methods can play a role in critical pedagogy, encouraging deeply reflexive accounts of participants' behaviour and knowledge. In policy terms however, this article concludes that it would be a risk for homelessness charities to utilise less stereotypical images in their fundraising materials, as the findings suggest such images align with those in the minds of potential donors.