Hey, heard you're looking for weird Vagabond headcanons and I am here to deliver. I've always thought the Vagabond be really good at sewing, cause of sewing up wounds and repairing his clothes. And this turns into making disguises for when he needs to lay low or go undercover. And when he joins the crew (and becomes closer to them) he wants to make (transwoman) Jack beautiful dresses, Rimmy-colored clothes for Jeremy. Now everyone in the crew has at least a few pieces made by him.