We examined whether the association of regional fat distribution with stress, defined in terms of vital exhaustion, and depression varies according to the total amount of body fat accumulation in healthy middle-aged men (n = 64). Regional fat distribution was measured using the waist-to-hip circumference ratio (WHR), and the total amount of body fat accumulation was measured using the body mass index (BMI). The results indicate that WHR in lean men was associated with characteristics contrary to those in moderately obese men. In lean men WHR tended to be associated with a high level of stress, while in moderately obese men an association was found with a low level of stress and a low level of depressive symptomatology. The present results support the suggestion that there is a difference between abdominal obesity at different degrees of generalized obesity, and they are likely to further our understanding about the differing risk for cardiovascular disorders posed by abdominal obesity in lean men compared to abdominal obesity in moderately obese men.