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Life course scholars have established that early life experiences are crucial factors in shaping developmental trajectories (Elder, et al., 2003). Early adolescent health has been one of the most widely studied of these factors (Wilson, et al., 2007; Forest and Riley, 2004), with increased attention on the long-term effects of obesity (Reilly and Kelly, 2011; Schafer and Ferraro, 2012; Raj and Kumar, 2010). While obesity is shown to be associated with several negative social and psychological outcomes (Wadsworth and Pendergast, 2014), less is known regarding how self-perceived weight affects individuals’ mental health trajectories through adolescence and young-adulthood (Ali et al., 2010). To address this gap, I use nationally representative longitudinal data to analyze how self-perceived weight affects self-esteem through adolescence and early adulthood. Consistent with previous literature (Greene and Way, 2005), I find that, on average, self-esteem increases through adolescence and young adulthood. Further, I find that weight perception is significantly associated with self-esteem trajectories for both men and women, but the effect is greater and more significant for women than men. Finally, whereas subjective weight perception has a significant negative association with self-esteem trajectories, body mass index does not; suggesting that individuals’ subjective weight perception influences self-esteem trajectories independently from objective weight measures. These findings are relevant for scholars and health practitioners and, in the conclusion of this article, the implications of these findings are discussed.