I think it could mean either that water lying on the ground soaked up through holes in the soles of his shoes, or that rain falling from above seeped down through holes in the upper part of his shoes (or both).
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Shelby KilluminatiDoes it mean that water is dripping down from somewhere top on his shoesNo. Rather, his shoes were worn so thin that his feet got wet when he walked on wet streets, as during rainy weather.