A drawer has an extra step. If it had no covering he could flick the shoes off on the edge of the container or a container he could stand in and remove shoes. Have the drawer low enough for space to do this. I do this and so the shoes I wear most frequently are on top.
I count the number of items I take with me, then try remembering before leaving places I go that I have that number of items. If handed something new the number goes up. I’m less likely to have a problem when I do this. I am an older adult though.
Did he have as much trouble remembering while medicated? Pausing to put it in memory and retrieveing from memory are all part of brain Executive functioning issues.