Hi Hailey As Jura says, normally you would use "the shoe.." or 'the boot..", and they mean, according to the Free Online Dictionary: "One is experiencing the same (often bad) things that one caused another person to experience." You can use 'jackboot' as a variation of this, but it has a much harder, and often more sinister, meaning. It implies a sense of oppression or threat, not just advantage. This is because the word 'jackboot' can be interpreted as a euphamism for an oppressive, military or fascist regime. So, "the jackboot is in the other foot" means that the oppressor becomes the oppressed and vice versa.

Hi the proverb is 'the shoe is on the other foot'. It means that one is experiencing the same (often bad) things that one caused another person to experience. Example 1: The teacher is taking a course in summer school and is finding out what it's like when the shoe is on the other foot, because he has been given a lot of home work.. Example 2: When the policeman was arrested, he learned what it was like to have the shoe on the other foot, because he felt afraid..