Angiosperms possess diverse sexual systems, often with different combinations of hermaphroditic, pistillate and staminate flowers. Despite this sexual diversity, most populations are either monomorphic or dimorphic with respect to gender strategy, where gender refers to the relative contribution that individuals make to fitness through female and male function. An important problem in evolutionary biology is to determine how and why variation in gender strategies originates and is maintained. Wurmbea (Colchicaceae), a genus of insect-pollinated geophytes, has recently become the focus of ecological and evolutionary studies aimed at understanding these issues. Phylogenetic reconstructions suggest dispersal from Africa to Australia, then New Zealand, and multiple transitions between monomorphic and dimorphic sexual systems within Australia. Microevolutionary studies of W. dioica and W. biglandulosa, two wide-ranging taxa with monomorphic and dimorphic populations, provide insights into the selective mechanisms governing transitions between sexual systems. Dimorphic populations of these taxa likely comprise independent origins of dimorphism via the gynodioecious pathway by invasion of females into monomorphic populations. Shifts in pollination biology and flower size, and their consequent effects on mating patterns, may have contributed to the evolution of gender dimorphism. Pollinator-mediated selfing and inbreeding depression provide a sufficient fertility advantage for females to be maintained in dimorphic populations. Once dimorphism establishes, increasing gender specialisation is associated with invasion of more arid environments. Inbreeding avoidance, particularly under stressful ecological conditions, is the most likely selective mechanism maintaining gender dimorphism in Wurmbea. We conclude our review by suggesting avenues for future research that might provide a more comprehensive picture of the evolution of gender strategies in Wurmbea.