I think that this art have a lot of symbolism into it..For example, hanging shoes..Shoe flinging is a way to get rid of shoes that are no longer wanted, are uncomfortable, or do not fit. Perfect metaphor for breaking up with someone. It may also be another manifestation of the human instinct to leave their mark on, and decorate, their surroundings. As Kevin by his music.
Yet another legend suggests that shoes hanging from telephone wires signal someone leaving the neighborhood onto bigger and better things. All these and the road that has no end are good way to freedom, for a new better life.
About shoes themselves: sneakers are unisexual, suits for a modern females and men. The same as Kevin's music. Boots as a symbol of country music. Some could see women's snickers with men's boot hanging on the same wire as a symbol of relationships. But as you can see they look in different sides.
It's all about the title "I Can't Hang with You Anymore."