I think almost all really good shoes are expensive. Sometimes you get lucky--I've got a cheap pair of satin flats from Payless that I've worn over and over without any problems--but the Vimes Theory is generally correct and if you CAN get the fifty-dollar boots, it is best to do so.

Sometimes I will end up wearing clothes from Walmart with a pair of shoes that cost over $200 retail (which will not be what I paid) and be happy, but it rarely works well the other way round--the only time I can think of in recent years was when I wore the Twilight dress with those little satin flats.