Maternal obesity is associated with significantly lower rates of breastfeeding initiation, duration and exclusivity. Increasing rates of obesity among reproductive-age women has prompted the need to carefully examine factors contributing to lower breastfeeding rates in this population. Recent research has demonstrated a significant impact of breastfeeding to reduce the risk of obesity in both mothers and their children. This article presents a review of research literature from three databases covering the years 1995 to 2014 using the search terms of breastfeeding and maternal obesity. We reviewed the existing research on contributing factors to lower breastfeeding rates among obese women, and our findings can guide the development of promising avenues to increase breastfeeding among a vulnerable population. The key findings concerned factors impacting initiation and early breastfeeding, factors impacting later breastfeeding and exclusivity, interventions to increase breastfeeding in obese women, and clinical considerations. The factors impacting early breastfeeding include mechanical factors and delayed onset of lactogenesis II and we have critically analyzed the potential contributors to these factors. The factors impacting later breastfeeding and exclusivity include hormonal imbalances, psychosocial factors, and mammary hypoplasia. Several recent interventions have sought to increase breastfeeding duration in obese women with varying levels of success and we have presented the strengths and weaknesses of these clinical trials. Clinical considerations include specific techniques that have been found to improve breastfeeding incidence and duration in obese women. Many obese women do not obtain the health benefits of exclusive breastfeeding and their children are more likely to also be overweight or obese if they are not breastfed. Further research is needed into the physiological basis for decreased breastfeeding among obese women along with effective interventions supported by rigorous clinical research to advance the care of obese reproductive age women and their children.