The song is recounting events experienced by the narrator while Christmas shopping. While waiting in a checkout line, a young boy ahead of the narrator talks about his wish to purchase a pair of shoes for his terminally-ill mother for Christmas, explaining that he doesn't have much time since she may pass away at any moment. Unfortunately, the boy does not have enough money for the shoes. The narrator, touched by this little boy's story offers to pay for the shoes to help the boy out.
"The Christmas Shoes" has been named on multiple lists of the worst Christmas songs of all time. In a voting bracket on Jezebel.com , "The Christmas Shoes" came up as the winner of being the "Worst Christmas Song".