I don’t know if all of these were intentional or not, but Over the Garden Wall has SO MANY Oz references- both to the MGM movie, and the original books. A lot of the designs bear resemblance to the Oz chracters (compare Adelaide’s hat to that of the Wicked Witch of the East- the ribbons are the same).
Jack Pumpkinhead was built in order to give the Wicked Witch of the North (Mombi) a great big fright. However, she used the Powder of Life on him and sure enough he became animated!
On his adventures, he regularly has to change his pumpkin in order to make sure he doesn’t spoil. He has a ritual of burying his heads so that their seeds might grow new ones for him.
He as built by a boy named Tip who was trapped in Mombi’s house, so I wanted him to look like he was constructed with whatever he could find. That’s why his gloves, scarf and boots are too big (as they belonged to the witch) and his clothes are too small (because they belonged to the boy).