Cliff Edwards's The Shoes of Van Gogh has this snippet about Pair of Old Shoes:

When the German philosopher Martin Heidegger saw the painting in an exhibition in Amsterdam in 1930 and was deeply moved, he used it as a demonstration of the meaning of a work of art in his essay "The Origin of the Work of Art," delivered as a lecture in 1935 at Freiburg. Heidegger wrote:

From the dark opening of the worn insides of the shoes the toilsome tread of the worker stares forth. In the stiffly rugged heaviness of the shoes there is the accumulated tenacity of her slow trudge through the far- spreading and ever-uniform furrows of the field swept by a raw wind. On the leather lie the dampness and richness of the soil. Under the soles slides the loneliniess of the field path as evening calls. In the shoes vibrates the silent call of the earth.

His essay goes on to say that the painting forces us to look at shoes devoid of their utility. Because we cannot put on these shoes in a painting, we are confronted by them in a new way. The work of art shows us a way of seeing apart from self-centered utility. But the art critic Meyer Shapiro attacked Heidegger's essay, concerned that Heidegger was searching for support for some Aryan "peasant-earth-and-blood" myth. As Shapiro notes, a peasant working in the wet fields would have worn wooden sabots; high leather shoes would have belonged to a city laborer. Derrida then joined the argument.

Derrida's joining is in his essay Restitutions of the Truth in Painting, where he writes:

As long we only imagine a pair of shoes in general, or simply look at them empty, unused as they merely stand there in the picture, we shall never discover what the equipmental being of the equipment in truth is. From Van Gogh's painting we cannot even tell where these shoes stand. There is nothing sorrounding this pair of peasant shoes in or to which they might belong - only an undefined space... A pair of peasant shoes and nothing more. And yet---

....In the shoes vibrates the silent call of the earth, its quiet gift of the ripening grain and its unexplained self-refusal in the fallow desolation of the wintry field. This equipment is pervaded by uncomplaining anxiety as to the certainty of bread, the wordless joy of having once more withstood want, the trembling before the impending childbed and shivering at the surrounding menace of death. This equipment belongs to the earth, and it is protected in the world of the peasant woman. From out of this protected belonging the equipment itself rises to its resting-within-itself.

A review of John Macquarrie's Heidegger and Christianity is a less dismissive than Shapiro, closer to Heidegger's insights than Derrida.

Heidegger is here thinking deeply into the nature of what is presented in Van Gogh's painting, thinking to experience the deep inner quiddity, the "existential inscape" of a simple pair of shoes. But this more active element in interpretation only follows on the initiative taken by the painting itself. As Heidegger expresses it, "the painting speaks." "If there occurs in the work of art a disclosure of a particular being, disclosing what and how it is, then there is here an occurring, a happening of truth at work." What Heidegger seems to suggest, comments Macquarrie, is that the discovery of truth is not just the result of human striving, does not involve ridding the psyche of all distorting influences so as to hear the truth plainly, but is an event "above and beyond our willing and doing" in which Being gives itself to be known. This is especially so in such a heightened mode of existence as art. "The essence of art," writes Heidegger, "is this: the truth of beings setting itself to work."

  ¶ 6:32 AM