Assessment in aesthetic fields presents a myriad of challenges in the higher education environment. This paper uses a metaphorical representation to explore the role of assessors within aesthetic assessment settings in higher education. It begins with a discussion of aesthetic fields and an exploration of the role of assessment in this area. Following this, the relationship between teachers and learners in aesthetic assessment settings is explored, as are some of the tensions that accompany assessment in aesthetic fields. This paper reports on a narrative and ethnographic study that explores the role of assessors in the context of aesthetically rich assessment tasks. The study, which uses five participants teaching in higher education settings, arrives at a metaphor which likens the assessors' role to that of an artistic curator or art critic. The students' place within that metaphor is also explored. Finally, conclusions are drawn about the nature of assessment in aesthetic fields and areas for further investigation identified.