Evidence suggests that men who strongly endorse masculine traits display an atypical presentation of depression, including more externalizing symptoms (e.g., anger or substance use), but fewer typical, internalizing symptoms (e.g., depressed mood or crying). This phenomenon has not been adequately explored in older adults or women. The current study used the externalizing subscale of the Masculine Depression Scale in older and younger men and women to detect atypical symptoms. It was predicted that individuals who more strongly endorsed masculine traits would have higher scores on the measure of externalizing symptoms relative to a measure of typical depressive symptoms Center for Epidemiologic Studies–Depression Scale. It was anticipated that results would differ by age-group but not by gender. Multigroup path analysis was used to test the hypothesis. The hypothesized path model, in which endorsement of masculine traits was associated with lower scores on the Center for Epidemiologic Studies–Depression Scale and with scores on the externalizing, but not internalizing, factor of the Masculine Depression Scale, fit the data well. Results differed significantly by age-group and gender. Masculine individuals reported lower levels of typical depressive symptoms relative to externalizing symptoms, but further research is needed within age- and gender groups. Results are consistent with the gendered responding framework and suggest that current assessment tools, which tend to focus on internalizing symptoms of depression, may not detect depression in individuals who endorse masculine traits.