Art displays life explicitly while blessing it. The aim of this study is to evaluate the interpretations of Meyer Schapiro and Heidegger through Van Gogh's drawing of shoes. Just like the two philosophers put it, the main question here is about who wears these shoes, a peasant or a townsman? In this context, one could get the impression that works represent daily life but the background about the life they depict gives them another quality. For this very reason, this paper aims to bring about a new interpretation - through Bataille-of shoes in Van Gogh's works together with an investigation into his style in other works.