This is our fifth child, "Buddy Boy." He is just a few months shy of being a fully independent two-year-old. As with most children his age, he is pretty sure that he knows what is best, and we, as his parents, don't have a clue. Actually, does that condition ever go away for kids?
Part of Buddy's all-knowing wisdom includes the fact that he must be wearing shoes at all times. And not just any shoes; no, they have to be the right shoes. Although he owns more than one pair, the only ones that will do are his church shoes, which he calls "shoe-on." He has decided that his "shoe-on" goes with every outfit, to include pajamas. Because seriously, would pajamas look good with tennis shoes? Of course not! No, only a nice pair of black shoes with a fake buckle (velcro, of course) will work with pajamas. And although his pajama top may not match the pajama bottoms, he just wouldn't feel right without his "shoe-on."
Buddy Boy's "Shoe-On"
And when we say he has to ALWAYS wear his shoes, we are talking ALWAYS! Including to bed. He will scream and shout if we try to put him to bed without his shoes on. So if you think it looks uncomfortable to sleep all night with your shoes on, that is just further evidence of the fact that you just aren't as wise and all-knowing as an almost-two-year-old!