I just got these and have only worn them to work once (breaking in). They hurt my ankles quite a bit. Even left sores on my ankle bones. They're pretty stiff out of the box, but they're leather so I'm confident they will soften with wear. DO NOT SIZE UP. On a friend's advice I bought my true size (US women's 7 in boots and sneakers) and they are perfect. I have a narrow-average width foot and I wear my casual shoes with minimal space in the toes, but these in size 7 left plenty of space for thick wool socks and room to spread my toes apart.