I used to wear Teva Mush flip flops, good running shoes, or a good sport sandal. However, I badly broke my leg just a few inches above my ankle last year and can't walk very much without the support of my running shoes now. My ankle hurts too much. So I guess I'll be the dorky looking tourist with running shoes on no matter what clothes I'm wearing. At least this will be true in Disney. I can still be somewhat fashion conscious when less walking is involved. If you have healthy ankles some really comfy and well broken in flip flops should be okay and look cute with sundresses.