The problem with shoes is that I just find them so ridiculously painful to break in. I have two pairs of Converse (green hi-tops with pink lining, orange lo-tops), and they both cause extreme pain to wear for more than a couple of hours. I have two pairs of ballet flats (pinky-purple with butterflies, brown with white polka dots), and they cause me so much pain that I can't even think about them anymore. I tried putting plasters (Band-Aids?) in strategic places on my feet before wearing them, but they still caused me to bleed. I wore the brown pair to a wedding, with plasters, and they hurt me so much that I had to wear slippers to rehearsal the next day. :/
So I wear boots! I don't know what it is, but I find boots much easier and less painful to break in. The only pair that took any real heavy breaking in were my New Rocks, and I just wore three pairs of socks for the first week and two pairs for the second, and it was fine. Or I wear Skechers. My feet *love* Skechers, I can break them in just by looking at them. :3
Note to self: buy more Skechers MaryJanes!