Since the discovery of brassinolide in the pollen of rapeseed, brassinosteroids (BRs) have consistently been associated with reproductive traits. However, compared to what is known for how BRs shape vegetative development, the understanding of how these hormones regulate reproductive traits is comparatively still lacking. Nevertheless, there is now considerable evidence that BRs regulate almost all aspects of reproduction, from ovule and pollen formation to seed and fruit development. Here, we review the current body of knowledge on how BRs regulate reproductive processes in plants, and what is known about how these pathways are transduced at the molecular level. We then discuss how the manipulation of BR biosynthesis and signaling can be a promising avenue for improving crop traits which rely on efficient reproduction. We thus propose that BR hold an untapped potential for plant breeding, which could contribute to attain food security in the coming years.