Originally Posted by usctrojans31
Don't do a driving shoe, especially Tod's...your feet will be so utterly painful by the end of the first day that your trip will be ruined. You need something with some arch support and a thick sole that will do well with cobblestone. My recommendation is a loafer in caramel/walnut and keep your trousers in the light grey range to fit in well.
Think Santoni Leonard as your style baseline. Yes, I know the color isn't what I suggested, but I am going solely for style.
Actually, those are a good suggestion though I'd probably take a pair of dark oak derbies or adelaides and a pair of black loafers for night. Another thought is to dump the black and shoot for tan or chestnut casuals instead. It gets more difficult if you want to wear shorts but there are decent enough flip-flops and sandals are seen all over Europe in the summer.
Driving shoes, as a form of slip on casual, are fine if the sole has sufficient structure to walk in. As others have pointed out, thin and soft soles lead to very sore feet and you'll do a lot of walking.