I've had these boots in black for almost 2 weeks now, and I love the way they're wearing. The elastic sides make these boots fit snugly, but they have a lot of give for easy on and off. My calves are on the average side, but I do think they'd work well for thin calves and larger calves. These boots have slouched a bit at the ankle, but I don't dislike it, and it isn't unexpected. The leather is soft and sturdy but it isn't stiff and it was inevitable that they would slouch. If you have very thin ankles then maybe you'd have an issue with bagginess. Again, I am average and I don't have an issue. I am 5'6 but with longish legs for my height. These reach the top of my calf and are well below my knee. If your legs are shorter, perhaps they'd hit at the knee. I have found myself wearing these boots with everything from jeans, leggings, and pants to dresses and skirts. There isn't an occasion where these aren't a good option. You can never go wrong with Cole Haan in terms of comfort and quality, and these are no exception. The sale price makes these a great value.