Im not big on the skirts .....i would wear very loose sweats, and slippers all the time but in order to feel normal i still wear jeans.(stupid yes. but it helps me mentally) socks. if i could go the rest of my life with out them I would and when I have to wear shoes they have to be super big on me. Im a size 101/2 but I am wearing a 13 1/2 daily when I go out when i get home socks and shoe come right off. I have to wear something on my feet cause the texture of the rug hurts and the hard wood flooring is way too cold. so I wear memory foam open backed slippers. as far as most comfortable.. if i could I would wear cotton silk or satin all the time. as far as the skirts comment I don't think my wife would approve. picture Homer Simpson in his moo moo!!!