This was a book in the Dr Seuss/PD Eastman format (i.e. about that size, not very long, line drawings with only a few colors) about a boy who starts noticing footprints on his ceiling and it turns out there is a boy who lives upside down. They make friends, but they can only go some places together. I remember a scene at a dock, for instance, where one was on top and the other was underneath. It has to have been published by 1964 or so.
Perhaps this might be The Boy on the Ceiling by Norman Bridwell, who also wrote the Clifford the Dog books?