Chile has experienced significant improvements in its economy; thus, a secular trend in height has been observed in its population. Gender equality has also improved hand in hand with active policies addressing the gender gap in several dimensions (work, education, health) and overall economic improvement. This study examined changes in sexual height dimorphism in four samples of Chilean male and female working-age subjects and attempted to establish associations with gender equality and welfare. Sexual height dimorphism was calculated and compared with gender equality and overall welfare indicators between 1955 and 1995. Sexual height dimorphism reduction was seen to be strongly associated with greater gender equality and some general welfare indicators, such as the infant mortality rate. Gross domestic product per capita was not associated with sexual height dimorphism, but it showed significant associations with gender equality indicators. Overall, the gender gap has been reduced in Chile, which can be observed through improvements in gender equality indicators and a reduction in height dimorphism, mainly in areas associated with women’s health. However, gender equality is still far behind in terms of female labour participation and women in political power, which require attention and further improvements.