These boots are very comfortable. I did not have to break them in at all and they seemed to fit right as soon as I took them out of the box. The fact that I can wear them folded down one day and all the way up the next day makes them very versatile, which I find really exciting, as I can wear them for multiple different occasions. These boots look great for a night out on the town with my girls and they keep me warm. I think they look best with a pair of jeans, but they can also be worn in the fall with a skirt. I would not recommend them for use in heavy snow, because they are not water proof so you don't want to stain the outside material. If you are going to be out hiking in the snow I would suggest you find a different boot that is waterproof. I love my Rampage Ashlee boots and I don't know if I could live without them. I'll probably try to pick up another pair in a different color this Christmas.