Sneaker saga

Cal is really hard on shoes - not sure what he does to them, but they only last a few months - the soles crack and the toes get severely worn and they basically fall apart.  But of course he never likes the new pair because they feel stiff and not broken-in.  We went through a massive search this most recent time, because he needs wide shoes, and there are no cool styles in wide.  I bought a larger size (in non-wide) but they weren't comfortable or practical.  We tried a shoe stretcher, but he said the shoes weren't any more comfortable after many hours with the stretcher applied to them.  We finally bought a plain white pair and decorated them with (expensive) stickers (which didn't stay on), fabric paint (which wore off immediately) and permanent markers.  But even after we decorated them, he insisted on wearing his old, falling apart, shoes.  He eventually had to switch, when the old shoes became unwearable, but this whole process will start again in a few months when the new shoes wear out.