I like to be barefoot and to wear flip flops, but thats not really fashionable, or is it? Which look better: open shoes (flip flops, sandals, heels) or closed shoes (sneakers, boots, running shoes) for a date or for an evening with your friends? Which look better on a girl guys?
Flip flops are only for the beach or the house. Sneakers and running shoes are for gym, except if it's stylish, like converses. The rest, sandals, heels and boots, are fine. The point is that your feet won't suffer though. If you walk in pain, you won't have a good time
It all depends on the outfit but if you are trying to look more business or even business casual, then don't go sneakers or running shoes. Boots can be both. Sandals are nice but not the cheap dollar ones from Old Navy unless you are going for a laid back look.