First things first, this shirt is true to size. Now I wouldn't wear it with leggings, simply because I I'm not comfortable in a shirt that doesn't come halfway down my thighs when I have leggings on. However, If you are comfortable in a shorter shirt with leggings, this would be really cute with leggings. It will cover most of your behind. The material, oh my, I could live in this shirt. It is so incredibly soft. It's not heavy, it's breathable. It is a light weight material so you might want a vest or sweater on those really cold days. I can't comment on it's durability yet. I've only washed it once. I will update this again as I wear it more. So far it has been great!