Over the past two decades, population-based studies employing semiautomatic computer-assisted programs have uncovered associations between retinal microvascular features and various systemic conditions. As the recognition of retinal imaging in cardiometabolic health grows, there is increasing evidence supporting its application in women’s health, particularly during the reproductive age. This review aims to summarize the indications of retinal imaging in women’s health and intergenerational health, where suboptimal retinal imaging has been found to mirror pathological systemic changes, such as suboptimal hemodynamic circulation, inflammation, endothelial dysfunction, oxidative stress, and hypoxia in vivo. Findings from Singapore Growing Up in Singapore Towards Healthy Outcomes and Singapore Preconception Study of Long-Term Maternal and Child Outcomes cohorts have reported serial changes in retinal conventional microvascular features (e.g., retinal arteriolar narrowing, retinal venular widening) and retinal geometric microvascular features (e.g., sparse fractal dimension, enlarged branching angle, and increased curvature tortuosity) during the preconception and antenatal phases. These morphological abnormalities were found to be related to female fertility, maternal antenatal health conditions, postnatal maternal cardiometabolic health, and intergenerational health in the fetus. Given the compelling evidence of the ability to detect microvascular changes through noninvasive methods at an early stage, retinal imaging holds the potential to facilitate timely interventions, mitigate the progression of complications, and prevent adverse pregnancy outcomes. Looking ahead, the convergence of artificial intelligence and advanced imaging techniques heralds a promising era in women’s health research and clinical practice.