Hum. Maybe up to ~$150? They'd have to be really damn good shoes, of course. The most expensive shoes in my arsenal closet so far are my sandals, my previous and current pairs costing around $100 each - mostly because it's hella tough to find the style I like in, say, K-mart :P Fantastically comfortable shoes I could stand for hours in I would consider a work/business investment at this point, particularly if they last forever (see: sandals).