Single-use packaging is one of the biggest contributors to plastic waste, and reuse has been identified as a key strategy to reduce such waste. However, reusable containers typically become worn, which may influence how consumers think and feel about reuse. The present research explored whether and how evaluations of a takeaway food service changed depending on the appearance of a reusable container. Two studies were conducted (using opportunity sampling) to (i) investigate the effects that signs of use have on people’s perceptions of reusable packaging systems using quantitative methods (Study 1) and (ii) understand the rationale underpinning these evaluations using qualitative methods (Study 2). Study 1 involved an online questionnaire where participants (n = 292) were shown images of reusable bowls for takeaway food with various levels of staining and asked to evaluate the container and the restaurant serving the food using rating scales. Study 2 involved in-person interviews where participants (n = 22) were given the opportunity to inspect either a clean bowl or a stained bowl and then were asked questions about the bowls. Signs of previous use seemed to undermine people’s willingness to reuse containers in the future and were associated with more negative evaluations of the packaging, product, and restaurant serving the food. These findings provide insights into the factors that affect people’s willingness to engage with reusable packaging systems, and we use these findings to suggest behavioural and design interventions that might mitigate negative evaluations and encourage reuse.