Very comfortable right from the start. I typically wear size 5.5 or 6 and ordered this flats in size 35.5. The fit was great but since I read from some reviews that it runs large for some ladies, I did go to the store to try on size 35 to check out the difference. My toes were pretty much pushed all the way to the tip of the flats in 35 so 35.5 was perfect for me with just sufficient toe room. I would suggest going for your smaller size if you're between sizes since the soft leather will most likely stretch with wear. Good quality leather and workmanship as well. It's so cute; I love it!