Metabolic syndrome (MetS) and its associated comorbidities has become increasingly prevalent on a global scale. Features of MetS (i.e., insulin resistance and obesity) have been studied in effort to reduce the likelihood of disease onset. Both obesogenic diets and stressful experiences impact metabolic regulation to variable degrees, where sex differences in metabolic programming, alongside environmental exposures, can alter the likelihood of disease progression. Thus, neurobehavioral, and metabolic changes associated with energy homeostasis may be attributed to inherent sex differences in endocrine physiology. Accordingly, our study aimed to further elucidate the sex-specific neurobehavioral and metabolic effects of both chronic obesogenic feeding and age-restricted stress experience. Our findings show that males were more responsive to obesogenic challenge than females, exhibiting increased weight gain, energy intake, fasting hyperglycemia, and insulin resistance. Further, they exhibited altered levels of endocrine hormones, anxiogenic behavior, and hepatic metabolic protein expression. Preliminary data also suggest that adolescent and adult stress exposure altered bodyweight and glycemia to variable degrees. These effects were both diet-dependent and sex-specific. Collectively, our findings implicate inherent sex-differences in adrenal axis physiology in the mediation of diet induced metabolic defects. The current study provides a framework to enable further investigation of the molecular relationships between stress, diet, and sex conditions to identify key factors that may determine the detrimental outcomes associated with MetS.