I think I got lucky with Rasta he's been wearing clothes since a week or two after I had him. I did start off slow with t shirts then, bandanas/neckties, then bows. When I first did it I would leave the clothing/accessories on for 30 mins then take them off. the next day a little longer wear and so on. He doesn't really like sleeves(feels too constricting to him maybe?). As long as the hood isn't covering his eyes he doesn't care. I haven't tried jammies but since you mentioned them I think it's time to do some shopping
