I think the suggestion to go for expensive shoes that last and are classic is a good one.
As for how to get those shoes cheap, shop sale racks at higher end stores (if you have a Nordstrom Rack around you, make it a regular stop). I make a habit of looking through shoe sale racks as much as I can - it will take a while to find good Born's, Dansko, Clark's, etc. and you can't be too picky regarding style when finding your first pair (once you have a pair or two, then you are just continuing to look for "cuter."
Also, find a good shoe store and try on a bunch. You may discover that Born is your brand, but you can't wear Dansko - that isn't unusual. You may discover that in a Doc Martin you are a 7 1/2 instead of your usual 8. Armed with that information, you can watch internet sales - but if you don't know, you spend a lot of time returning shoes to Zappos.
For something a little dressier, I like Sofft.