I have a general klal (disclaimer: it has some [read: very, very few] exceptions):
Only buy shoes from established shoe companies. Not designers.
Examples of established shoe companies: Johnston & Murphy, Ecco, Florsheim, Mephisto, Bruno Magli, Allen Edmonds, etc.
Examples of non-shoe companies: Kenneth Cole, Hugo Boss, Ferragamo, Banana Republic, etc.
Safek: Cole Haan, Rockport, Aldo (technically all they do is shoes but it's junk IIRC), etc.
Yes, you can get a cool looking pair of Kenneth cole shoes on sale for about $120 but if you would spend $160 on a real shoe brand what you get for the extra 33% is probably 6 more months of wear, better comfort and support, and often the shoes look better past the 1 month mark (leather doesn't peel etc.).
p.s. For me the hardest part about shoe shopping is finding the style I like (slightly european style) in a real shoe company in the U.S. for under $100-160ish. If you are picky about style it can be a challenge.