I have searched high and low for a casual yet non-clunky looking boot to wear with jeans and finally found it here. I wear size 9.5 - that's what I ordered and they fit perfectly - the toebox is fairly square so there's ample room for a wider forefoot, yet they don't slip off my heels. I was concerned with my size foot that a boot would look huge, but my first reaction when I pulled them out of the box was that I must have ordered the wrong size, cuz they didn't look big enough for size 9.5. They are also a little darker than in the big picture, but a good dark. I was so glad to finally find a boot that has plenty of cushioning, not only in the heel, but also in the forefoot where I need it even more. And they also have good arch support. My only concern is how the finish will wear, but after two long days of wear, they look fine.