But, Im making an assumption since the item is boots that you have most of it weight painted and using the cloth sim for only certain parts of the boots. i.e. the top folds
If that’s not the case make sure that collision is turned on (on the character and not the boots), and then check to see if it is not pinned to something else.
You’ve probably checked those two, but I’m just trying to help you work through this issue. It should work as you describe on a static cloth object.
I like to parent with all my cloth sims so the items stay aligned at the starting frame, even if I move said items.
Side Note: I don’t think having the entire boot simmed for cloth will give the desired effect you’re looking for.
A weight painted boot with the folded over leather section set up as a cloth sim would be the idea setup for this.