He does usually wear a kippa now--that was one of the big milestones we hit over Pesach. All the other men and boys in the house wore one, and Barak had his new excavator kippa, so he started wearing one automatically. If he drops it, he exclaims, "My kippa!" and puts it back on. If he realizes he's not wearing, he'll ask for it; if I tell him he's not wearing it, sometimes he'll ask for it, although sometimes not. And if I just plunk it on his head, he says "Thank you," and adjusts it how he likes it--back on his head.
Black velvet kippa, back on his head, with his name. And payes. And an excavator. He's going to be the frummest construction worker in town.