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1.
1. A thick military boot.
2. A common epithet, used to conflate someone with Nazism.
"I am still without any clear information as to what a jackboot is. It is a kind of boot that you put on when you want to behave tyrannically: that is as much as anyone seems to know."

-George Orwell
by nedlum February 13, 2006
 
2.
Thoes cool boots the Nazi's use to goose step with
Jackboots are used for heiling and marching
by The Col. November 27, 2004