Floral monosymmetry and asymmetry are traced through the angiosperm orders and families. Both are diverse and widespread in angiosperms. The systematic distribution of the different forms of monosymmetry and asymmetry indicates that both evolved numerous times. Elaborate forms occur in highly synorganized flowers. Less elaborate forms occur by curvature of organs and by simplicity with minimal organ numbers. Elaborate forms of asymmetry evolved from elaborate monosymmetry. Less elaborate form come about by curvature or torsion of organs, by imbricate aestivation of perianth organs, or also by simplicity. Floral monosymmetry appears to be a key innovation in some groups (e.g., Orchidaceae, Fabaceae, Lamiales), but not in others. Floral asymmetry appears as a key innovation in Phaseoleae (Fabaceae). Simple patterns of monosymmetry appear easily “reverted” to polysymmetry, whereas elaborate monosymmetry is difficult to lose without disruption of floral function (e.g., Orchidaceae). Monosymmetry and asymmetry can be expressed at different stages of floral (and fruit) development and may be transient in some taxa. The two symmetries are most common in bee-pollinated flowers, and appear to be especially prone to develop in some specialized biological situations: monosymmetry, e.g., with buzz-pollinated flowers or with oil flowers, and asymmetry also with buzz-pollinated flowers, both based on the particular collection mechanisms by the pollinating bees. Floral monosymmetry has developed into a model trait in evo-devo studies, whereas floral asymmetry to date has not been tackled in molecular genetic studies.