subject: Origin of Sayings: 'Boot on the Other Foot' [print this page] Wearing the boot on the other foot is a saying that is tangible compared to wide calf boots. From my perspective it points towards the worst situation were the accuser or oppressor is experiencing the worst or the side of the underdog. This is something that you will not want to experience as the oppressor or accuser, especially if you do not know what that particular person is going through or feeling. In some situations if someone is saying negative things about a person that has not done anything and just hates them and puts their name in the dirt means that the person that is doing the talking will soon experience the pain that the non accuser is experiencing. That is scary because wide calf boots are larger than the orignal which usually makes the situation worse for the oppressor.