weighing my options

Chicago winter is approaching, and i'm well into my winter clothing prep with several jackets, cloaks and accessories stashed away, but appropriate footwear is sitll top on that list.  a couple options i'm considering...

the Chooka bootie.  so happy to find a shortie rain boot option, and double points for not being a pair of Hunters.  but, will they be warm in -20?

these furry boots are my dream.  ash yeti knee highs, that would probably take more maintenance to keep them looking nice than my own hair.  but they would look sooo good stomping around the snow packed streets.

these sam edelman jayla booties kill.  they look stylish, and like they could stand up to a brutal winter.  but, will my calves get cold?

options.