#9: Jileon Extra Wide Calf Rain Boots at Amazon, $89.95
This rain boot from Jileon fits up to a 21″ calf and are made from durable rubber to ensure they are definitely waterproof. According to the customer reviews, the size 8 fits a 19.5″ calf with extra room to spare. Another customer said her calves were 21″ and the boots fit her calves with room to spare.