I usually wear an 8WW, but often can make do with 8.5W. My forefoot is very wide and I have a high arch. I have a 16-inch calf.

I bought these boots in 8.5E because that is the size that was on sale. For the price, they are a decent boot. The material is VERY stiff, but it does break in over time. They look good and I've gotten compliments on them.

The boots do run short and because of that were tight in the toe box for me. I probably would have been a little more comfortable in a 9WW, but decided to keep the 8.5W because I would have had to pay more for the other size.

As for the calf circumference, it is perfect. There's just enough room to stick pants in them (and I don't just mean skinny pants), but they look normal if I'm just wearing them with tights/pantyhose.

I have walked about 2 miles in these boots in one shot, and besides being a little cramped in the toebox, they were very comfortable and up to the challenge. They do not have a ton of support, but I prefer that. If you're looking for a lot of arch support, try another boot. They do not have much tread either, so be careful on ice.