on one's uppers

From uppers (“the top part of a leather shoe”), having worn through the sole.

on one's uppers

1. destitute; poor.

   Synonym: down on one's uppers

   • 1902, Guy Wetmore Carryl, How a Cat Was Annoyed and a Poet Was Booted:

     “We are bound toward the scuppers,
     And the time has come to act,
     Or we’ll both be on our uppers
     For a fact!”