So true story me and a few friends had a game we played every Friday in highschool. One player played a tiefling rogue and his catchphrase was "Dont piss me off I'll steal your pants" (which when stated for the nintieth time was annoying). Anyways about half way through the session we were on a barge traveling to an island near the coast we decide to take a break and agreed our players would take a long rest. It was at this time I pulled our DM aside and said to him "I'd like to steal our rogues pants" he laughed and told me to roll with no bonuses (I was a ranger). Nat. 20. His pants were mine. I then told everyone on break (except the rogue) that I had his pants he knew something was up and would frequently ask to make checks to notice what was wrong. The DM called a low roll for it but some how even with his active perception he couldnt notice it. This went on for the entire session until a madman yelled at him for being half nude in public. It was at this time the DM made him make a final roll to recognize the issue. Nat. 1. Not only were his cheeks feeling the breeze he was adamant he was in fact wearing pants and the madman was just delusional. It was at this point I gave them back.
As a bonus he never threatened to steal anyones pants again.