Postpartum weight retention (PPWR) is a significant contributor to the development of overweight and obesity in women of childbearing age. Stress may be a key mechanism making it more difficult for mothers to lose weight in the year following delivery. The aim of this study was to assess whether specific aspects of parenting stress and life stress influence postpartum weight retention in new mothers. Women in late pregnancy or up to 2 months postpartum (n = 123) were enrolled in the study and followed through the first year postpartum. Linear regression models evaluated the associations of parenting stress (isolation, attachment and depressive symptoms) as well as overall life stress at 2, 6, and 12 months postpartum with PPWR at 6 and 12 months. During the first year postpartum, higher depression and life stress were significantly associated with greater PPWR. As the effect of depression diminished, the effect of life stress became significant. Contrary to hypothesized relationships, fewer problems with attachment and less social isolation were significantly associated with greater PPWR. Higher gestational weight gain and African American race were also significantly associated with greater PPWR at both 6 and 12 months. Different types of stress predict weight retention in first time mothers during the first year postpartum. Understanding the relationships between parenting stress, concurrent life stress and PPWR can enhance the development of future interventions that specifically target self-identified stressors, leading to improved weight related outcomes.