Lol @ Deb.
It depends on the shoe and what I need it for. My baseline level of comfort for an all-day shoe is different from an evening 'sitting' shoe (i.e. something I'd wear to go out to dinner and a movie). Like Ummlila, I won't wear ugly shoes just because they are comfortable. I also won't wear really uncomfortable shoes just because they are pretty! But I'm lucky that I have relatively unfussy feet, so having to trade beauty for comfort is not and issue for me just yet. I can always find stylish shoes that are all-day comfy.
As for evening shoes -- which for me means high heels -- well, that's different. They have to be comfy to walk around in for about two hours. I was not a high-heel wearer in my youth, because in my neck of the woods, 'fancy' shoes were a bit gauche. I finished high school right as the grunge movement got going, and lived very close to the grunge epicentre of Seattle. And to add to this, I was studying biology (a 'crunchy' discipline) at a very left-leaning university. Looking 'done up' was not something we EVER did! Plus, the general wisdom was that 'all high heels are painful and destroy your feet'. In my mid-twenties, I did have a couple of pairs of lovely high-heeled sandals that I bought to wear to weddings, but these were super uncomfortable and I so I assumed that the general wisdom was correct.
It turns out that this is just a persistent myth. You CAN have heels that are comfortable, but you need to search and you need to pay. Well-made shoes cost more, generally. They shouldn't pinch or rub. What they can do, no matter how good they are, is cause aching arches by the end of a long evening of standing around, but that's simply because the heel forces my foot into a steep angle, and of course my feet don't appreciate that. But for moderate periods of time, good-quality, comfortable high heels are totally reasonable.
