What values and choices does Charlie make when wearing the old boots and the shiny boots?

The boots Charlie wears in Runner represent the double lives he leads. The pair of hole-filled, oversized boots Charlie inherits from his father are a symbol of Charlie's physically uncomfortable but honest life as a poor person. By contrast, the well-fitting shiny leather boots Squizzy provides Charlie represent his physically comfortable but morally bankrupt life as a well-paid criminal associate. As Charlie trades out the pairs, leaving the nicer pair at Squizzy's in order to pretend to his mother that he didn't take the job as a runner, Charlie finds that each pair has its tradeoffs. For a long stretch of the novel, Charlie wears his comfortable pair home, in a symbolic gesture that conveys he no longer cares what his mother thinks about him. Despite this, ultimately Charlie decides to give back his nicer boots to Squizzy and return to his honest boots and honest life.