I am a total wimp when it comes to shoes. I started with the birks, but then they started feeling too hard. Switched to Dansko clogs and liked those for quite a while. Now I switch between Soft Spots loafers and Clarks sandels.
My softspots are something like this:
http://store.nordstrom.com/product/p...tyleID=2844431
My opinion is that most people, particularly women, are wearing shoes that are too small and too tight on their feet. I always thought I wore a size 9W but sometimes could wear a 9B. Now, after two babies and having really sensitive feet, I wear a 10.5 - 11, wide or double wide, depending.
I highly recommend going to a real shoe store, where they actually measure your foot and where they intelligently choose styles that would work for you. These kind of stores are hard to find, but well worth the effort!