I have yet to wear these in the rain so this is strictly an out of the box first impression of the Grey KiKi Spot patterned boot. Do they run large? That does seems to be the case. I wear a 9.5 and there is room even with thick fuzzy socks, but not so much room that its worth exchanging. An 8.5 would have been perfect if that size existed.  Are the ankles big/roomie? Yes, but not any bigger than your average rain boot. Its not supposed to fit like a riding boot. It fits like a sleek looking womans rain boot. I had zero issues with the calves being too tight. My calves are 14 inches in circumference. There is about 1.5 inches in extra room from my shin to the front of the boot opening.  I would have liked less extra room but again, this is a rain boot and not a fitted riding boot/I have thin legs. I was looking for a cute womans rainboot that didn't make me look like a 5 year old wearing my dads boots and I got what I wanted. Would purchase another pair in a different pattern if my finances allowed! First thoughts as I pulled them out of the box? Sturdy, feminine, great quality, fun, expensive look for less.