Maybe you don't value $300 sneakers and see it as wasteful? I do. But, I'm sure this guy would shake his head at someone buying a $2,000 laptop (or something like that) when there is one for $1,000 that is "just as good."
I don't know. Those shoes look awfully comfortable and make him look clean. Perhaps they are a very valid business expense and well worth the money: Perhaps he did A/B tests with different shoe styles and manufactures? Perhaps the shoes are a topic of conversation during the sale that he can switch to and then back to close a deal? Perhaps if his feet don't hurt after 11h and he's able to hustle that one more hour, the shoes pay for themselves.