I'm not really a cheap ass when it comes to my shoes. I rock Ecco City Austin slip on's they are nice enough for work (teaching at university) and good to wear casually.
If you have something that you love in style but dislike in comfort, I recommend SOLE heat moldable insoles, you thorw them in the oven then stand on them and they fit your arch perfectly. I use a pair in my hiking boots and they make a huge difference.