You can get a cheaper suit and have it tailored for a better fit and look great. You can get away with a shirt that’s slightly unfitted if it’s under your jacket. You can wear cheaper neckties and pocket squares and still look put together. But you can’t wear cheap shoes and have it not look completely noticeable. Rubber soles are obvious on an “oxford” and look cheap and wear terribly. Bad leather not only hurts to wear, but wears badly. And you don’t really know the difference between a quality shoe sole and a bad shoe sole until you’ve broken in a pair of decent shoes that conforms to your feet. I think a lot of people hate to wear their dress shoes because they claim it make their feet hurt. I think they’re just buying bad shoes to begin with, because if you have a good pair of dress shoes, you’ll want to wear them all the time. It’s like your baseball mitt for your feet — fits perfectly and gets better with age.