The Doctor once went as Sam to a Halloween party and was unhappy to find out that no-one recognised who he was. It wasn’t until later that he realised they hadn’t heard of the Winchester Gospel on Catrigan Nova.
Dean had once kitted the Doctor out in some clothes he’d found in one of the TARDIS wardrobes, and then given him hunting gear. The stakes were the Doctor’s own choice as he was convinced that was how you kill vampires
The Doctor writes his name on the inside of all of his Converse, after a mishap on a bouncy castle where someone stole his shoes.