Not sure how this could be implemented, but several times this has come up: I want to release a prisoner with specific items.
First case: A space-refugee arrived, but she was a 75yo Luciferium addict. The colony had no way of handling that kind of an issue, so chose to release the prisoner. She arrived with 4 doses of Luciferium, and I would have been quite happy to let her keep them -- bad enough as a Luci addict, but to be kicked out with no doses in your pocket is scary. Unfortunately, there was no way to do this.
Second case: In a feud with a local tribe, they send raiders. We'd be really happy to send one of them home with one of his kidneys in a box with a nice red bow tied around it. (Thanks, Maniak!)
+1
Personally wish I could force attire on prisoners as well.