To be on one's uppers means to be impoverished, down-and-out or shabby-looking. To be down on one's uppers is a variation with the same meaning.
It is of U.S. origin and dates back at least to 1891 when it was recorded in The Century Dictionary.
The uppers are the upper leathers of shoes or boots; a person “on his uppers” has worn through both sole and welt. Footgear as indicative of financial status is also found in the term well-heeled meaning well-off (though this is probably of unrelated origin), and in down-at-the-heel.
That was interesting, thank you!
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