on one's uppers
on (one's) uppers
Having no money; broke. The phrase was originally used to describe people who were so poor that they had worn their shoes down to the uppers (the part of the shoe above the sole). I'm down on my uppers this week, so can we go out for drinks next week, after I get paid? My mother was always slipping money into the hands of our friends she thought were on their uppers.
on one's uppers
Poor, in reduced circumstances, as in as in The Smiths try to hide the fact that they're on their uppers. First recorded in 1886, this metaphoric term alludes to having worn out the soles of one's shoes so badly that only the top portions remain.