To investigate maternal characteristics associated with breastfeeding initiation and success. Women enrolled in the Mothers Outcomes After Delivery study reported breastfeeding practices 5-10 years after a first delivery. Women were classified as successful breastfeeding initiators, unsuccessful initiators, or non-initiators. For the first birth, demographic and obstetrical characteristics were compared across these three breastfeeding groups. For multiparous women, agreement in breastfeeding status between births was evaluated. Multivariate regression analysis was used to identify characteristics associated with non-initiation and unsuccessful breastfeeding across all births. Of 812 participants, 740 (91%) mothers tried to breastfeed their first child and 593 (73%) reported breastfeeding successfully. In a multivariate analysis, less educated women were less likely to initiate breastfeeding (odds ratio (OR) for non-initiation 1.97; 95% confidence interval (CI) 1.23, 3.14). There was a notable decrease in breastfeeding initiation with increasing birth order: compared to the first birth, the odds for non-initiation after a second delivery almost doubled (OR 1.83, 95% CI 1.42, 2.35) and the odds for non-initiation after a third delivery were further increased (OR 2.44, 95% CI 1.56, 3.82). Successful breastfeeding in a first pregnancy was a predictor of subsequent breastfeeding initiation and success. Specifically, women who did not attempt breastfeeding or who reported unsuccessful attempts to breastfeed at first birth were unlikely to initiate breastfeeding at later births. Cesarean delivery was not associated with breastfeeding initiation (OR 1.01; 95% CI 0.68, 1.48) or success (OR 1.33; 95% CI 0.92, 1.94). Breastfeeding practices after a first birth are a significant predictor of breastfeeding in subsequent births.