A yellow shirt
A green shirt
A matte black shirt
and you are holding only the yellow shirt, you can 'drop shirt' and it will drop the yellow shirt on the ground.
However, 'wear', 'remove', and 'hold' don't act that way. If you have only the yellow shirt in your inventory, 'wear shirt' will kick up a 'which shirt' error, as will 'hold shirt', 'lower shirt', and -- if you were wearing the yellow shirt -- 'remove shirt'.
It would be awfully cool if all of those commands used the same 'inventory only' checking as drop does. I don't know how hard that is to code, though.