Unlike studies conducted in Western countries, two studies among Black South African men who have sex with men (MSM) found no support for the association between gender nonconformity and mental distress, even though gender-nonconforming men experienced more discrimination and discrimination was associated with mental distress (Cook, Sandfort, Nel, & Rich, 2013; Sandfort, Bos, Knox, & Reddy, 2016). In Sandfort et al., gender nonconformity was assessed as a continuous variable, validated by comparing scores between a categorical assessment of gender presentation (masculine, feminine, no preference). Using the same dataset, we further explored this topic by (1) testing differences between gender expression groups in sexual minority stressors, resilience factors, and mental distress; (2) testing whether the impact of elevated discrimination in the feminine group was counterbalanced by lower scores on other stressors or higher scores on resilience factors; and (3) exploring whether relationships of stressors and resilience factors with mental distress varied between gender expression groups. Controlling for demographics, we found several differences between the gender expression groups in the stressors and resilience factors, but not in mental distress. We found no support for the idea that the lack of differences in mental distress between the gender expression groups was a consequence of factors working in opposite directions. However, internalized homophobia had a differential impact on depression in feminine men compared to masculine men. In our discussion of these findings, we explored the meaning of our participants’ self-categorization as it might relate to gender instead of sexual identities.