Flowering plants are able to develop gametes throughout their lives. As a consequence, environmental conditions can impact this development and alter a plant's functional gender or the degree to which it achieves fitness through male or female function. Two dimorphic breeding systems are widespread among angiosperm families: gynodioecy (hermaphrodites and females) and dioecy (males and females). Gynodioecy can evolve into dioecy, via loss of female function on the hermaphrodites, or it can remain stable. Here I discuss how developmental plasticity of gender can impact the sex ratio of populations and thereby influence the transition of one breeding system into another. I review studies showing that greater plasticity of fruit production by hermaphrodites as compared with females causes sex ratios among populations to vary in response to environmental conditions, with higher female frequency expected in harsh or low-quality sites. I also review how dioecy may evolve in dry sites to avoid inbreeding and any consequent inbreeding depression. Taken together, these studies show the importance of understanding how ecological development affects functional gender and consequently the evolutionary stability or malleability of dimorphic breeding systems.