A client of mine just posed this question to me and it's one I hear SO often. You don't want to have to suffer in the shoes you wear, you want them to be comfortable, functional but for the benefit of what I do...please let them be stylish.
The key point is this: You are what you wear..if your shoe is chunky and clunky, square and boxy,
that's what it will do to your overall look. It will make you look, chunky and clunky.
You want sleek, stylish and fashionable but STILL comfortable!
Ever seen a woman in uncomfortable shoes? I bet you never noticed much more about her outfit.
Do you see how the shoe on the left, though still a fun color is more visually heavy and clunky looking vs. the shoe on the right? Both are from a comfort brand and both are intended to be a comfort shoe.
So if you had a choice, would you want your look to be chunky and clunky or sleek and stylish? It's just a matter of choice. Truly.