Ah I understand completely. I never wear athletic sneakers unless I'm doing actual athletics/working out. I don't really wear shorts but I often wear skirts and here are some of my favorite shoes that I own for walking around (since I don't have a car and therefore have to walk most places):
Puma does a comfy and cute ballet sneaker once you break them in:
http://www.zappos.com/product/7477727/color/173798
These Sanuk shoes are really light and comfy and nice with skirts:
http://www.zappos.com/product/7395250/color/3?zlfid=111 (I've also had Sanuk flip-flops which I've found more comfy than the regular kind)
The MOST COMFORTABLE FLIP-FLOPS I've ever worn are Birkenstocks. I've for years said that they're not the most attractive shoes but I got these as a gift and I'm a convert. They look and feel kinda like a flip-flop but are so much more comfy and have loads of support:
http://www.zappos.com/birkenstock-pi...ky-suede-black