Assessing patient decision-making capacity while adhering to the requests of patients with mental illness remains a great ethical challenge. In patients with severe mental illness, the assessment of decision-making capacity can be difficult, particularly when a care team is also trying to navigate cultural, educational, and linguistic barriers. It becomes especially complex in situations where the patient is not only diagnosed with a severe mental illness but also suffers from a comorbid medical illness that the patient refuses to have treated appropriately. Balancing patient wishes while respecting patient autonomy creates further issues when assessing decision-making capacity. As such, the following case presents a transgender man who suffers from schizophrenia with a persistent skin infection on the patients torso secondary to wearing a brassiere for an extended period. This case report addresses the intricacies surrounding patient decision-making capacity, specifically in the psychiatric population.