I was at Sanctuary and gave a settler a customized pipe gun, ammo, and raider leathers, which seems to freeze the game.
It was a new settler, and I do remember giving him armor at some point (I really don't remember).
I came to fast travel back to Sanctuary to give him a new weapon, and when I put the raider leathers in his inventory and press Y (XBOX One) to equip it on him, the game just buzzed and froze.
I guess it is some sort of corrupt settler or that there is already armor on him? It looks to be that the settler is topless but has his default or leather pants on.
EDIT: I tested it with the same exact raider leather and it didn't happen to anyone else when I tried equipping it on him, and before the game crashed, there was no already preexisting armor that I identified in his inventory, though it could be hidden due to a bug.
This video is on PC from someone I searched up, but it's basically what I did to crash that game, and also like this guy's video, mine is reproducible on that specific settler. Keep in mind i'm on Xbox One.
https://www.youtube.com/watch?v=xpoR6TOSvOE
SECOND EDIT:
I guess when I equip raider leather on ANY settler (in this case I tried my first one at Starlight Drive In) the raider leather in HIS inventory disappeared after pressing Y to equip it on him. Out came his farming clothes. I put the farming clothes back on him and then the raider leather re-appeared in his inventory again.
I think this was put on the Fallout 4 Wikia article of an extensive list of bugs, but was only listed for PC. This happened on Xbox One as well and seemed to match the Wiki's description that the game would freeze or crash if the same clothing was put onto an NPC, in this case, raider leather. Glad I could find the reasoning behind the crash myself.