The inflorescences of Solanaceae are unique and complex, which has led to long-standing disputes over floral symmetry mainly due to different interpretations of the cyme-like inflorescence structure. The main disagreements have been over how the phyllomes associated with the flower were arranged relative to the inflorescence axis especially during early flower initiation. Methods: Here we investigated the evolution of inflorescences in Solanaceae by analyzing inflorescence structure in the context of phylogeny using ancestral state reconstruction (ASR) to determine the evolutionary transitions between loosely arranged and tightly clustered inflorescences and between monochasial-like and dichasial-like cymes. We also reconstructed two-and three-dimensional models for 12 solanaceous species that represent both inflorescence and phylogenetic diversity in the family. Results: Our results indicate that the most recent common ancestor of Solanaceae had a loosely arranged and monochasial-like cyme, while tightly clustered inflorescences and dichasial-like cymes were derived. Compared to the known process of scorpioid cyme evolution, Solanaceae achieved their scorpioid cyme-like inflorescences through a previously undescribed way. Along the pedicel, the two flower-preceding prophylls are not in the typical transverse position of dicotyledonous plants; they frequently have axillary buds, and the main inflorescence axis continues in a sympodial fashion. As a result, the plane of symmetry of the flower is 36°from the median, and the inflorescence axis and the two flower-preceding prophylls are symmetrically located along that plane. Conclusions: A better understanding of the morphological evolution of solanaceous inflorescence structure helped clarify the floral symmetry of Solanaceae.