I find the fact that Obama never got his shoes resoled after winning the Presidency to be a much larger view into his character.
He could take the time out to go get it done. Hell, he could get an aide or an intern to do it. He could have Michelle mail order shoes. He could have a cobbler from Milan fly in and personally make him a brand new pair of $5,000 oiled leather sabegos.
But he has more important things to do than worry about a hole in the bottom of his shoe.