On your uppers
Q From Eleonora Corvin: Can you tell me what the expression on your uppers refers to? I saw it used to signify someone in dire straits and would think being down more appropriate than being up.
A The uppers here are the bits that cover the upper part of a boot or shoe. The implication is that the soles have worn out and that the person concerned is reduced to a pair that consists only of uppers — quite useless, of course — and that he or she is too poor to be able to replace them.
The saying appeared in the eastern US in the 1880s. To judge from the early examples, it was originally a bit of actors’ slang (hardly surprising, as it is a notoriously uncertain profession, more full of people down on their luck than almost any other). The first form was walking on my uppers, which gives the sense behind the saying more clearly than the later abbreviated version. Here’s an actor in a story by Brander Matthews, in Harper’s New Monthly Magazine of October 1896: “I was going to give my two weeks’ notice; and I’d have done it, too, but ... I didn’t want to come back here walking on my uppers”.
The incongruity between uppers and being down must have been a large part of the inspiration for the saying. One version, in fact, makes this explicit by describing somebody who is impoverished as being down on his uppers.