From an evolutionary perspective, art presents many puzzles. Humans invest substantial effort in generating apparently useless displays that include artworks. These vary greatly from ordinary to intricate. From the perspective of signalling theory, these investments in highly complex artistic designs can reflect information about individuals and their social standing. Using a large corpus of kolam art from South India (N = 3139 kolam from 192 women), we test a number of hypotheses about the ways in which social stratification and individual differences affect the complexity of artistic designs. Consistent with evolutionary signalling theories of constrained optimisation, we find that kolam art tends to occupy a ‘sweet spot’ at which artistic complexity, as measured by Shannon information entropy, remains relatively constant from small to large drawings. This stability is maintained through an observable, apparently unconscious trade-off between two standard information-theoretic measures: richness and evenness. Although these drawings arise in a highly stratified, caste-based society, we do not find strong evidence that artistic complexity is influenced by the caste boundaries of Indian society. Rather, the trade-off is likely due to individual-level aesthetic preferences and differences in skill, dedication and time, as well as the fundamental constraints of human cognition and memory.