This boot does indeed fit tight on the calves and loose around the ankle. That was the look I wanted, more of a less fitted, straight up-and-down shape, so they were perfect. I always thought I had more athletic calves (about 13") but I guess according to some other reviews that's considered skinny? Anyway, the tops of these boots are tight enough to stay up on my bare leg, but still have enough room that I can tuck in skinny jeans as well. These have just enough western details that they don't look like more prim, classic riding boots, but are simple enough that they don't look too cowboy either. I ordered the black and the leather had a bit of sheen to it, not matte, and lots of distressing. I found they fit true to size, though if you plan on wearing them with thick socks, I would size up due to the pointier toe. They were comfortable right out of the box. I would have given these five stars, except one side has developed a bit of a squeak in the heel. Annoying.