Did capt James T. Kirk ever wear a red shirt?

That's a fun question! While it's true that red shirts were famously associated with peril on the original Star Trek series, Captain Kirk *never* wore a red shirt.

* Command Crew: Kirk, Spock, and McCoy all wore different colored uniforms to distinguish their roles: Kirk wore a yellow shirt, Spock blue, and McCoy green.

* Red Shirts: The red shirts were worn by the bridge crew, security, and other non-officer personnel.

So, while Kirk might have occasionally been close to wearing a red shirt, he never actually donned one. He was too important to the story for that!