I wear 8 in sandals and 8.5 in closed toe shoes. Ordered a 9 in these and the fit is perfect. I have flexible flat feet and foot pain so I am over hauling my shoe wardrobe. These offer structure and are fairly comfy. They are not cushiony soft but are not hard. These are not a dressy boot but still look okay with a denim skirt or casual type dress. Their versatility is limited, also, because they cannot be worn under jeans or pants, unless the legs are wide, because of the bulk of the shaft. They are very warm and make a good winter boot. My office is cold and these kept me warm. They are not the cutest boots ever but aren't too goofy looking! I am glad I kept these as they will make a good winter boot. Plus, I feel so tall but not like I am wearing high heels.