A. Yes!!! It feels impossible when we are looking at negative digits for tomorrow in Chicago, but it can be done! For starters, the girl on the left is a don't! On the right, a do. You have to start with a hat. Try to get many different styles. I love the one on the blond and it can be worn to cover your ears (so important!). I also love a great skull camp pulled down tight and the page boy hats are cute too (but not very practical).
The second thing you have to think about is a cute coat. But in super cold weather, warm is more important that cute (yes, I said that. I, who usually says "fashion over function always!"). There are a ton of great, puffy, warm coats out there. Black is always good but take a look at white or silver. Belted is great, will give you the look of a waist even though you are wearing a puffy coat. When it's not that cold out a wool, belted pea coat is darling. Layer if you think you need to for more warmth and always add a cute scart. Pull colors from the coat and hat.
And a boot!!! Not easy to find cute and practical but in super cold, super snowy days go with waterproof!!! I love my Uggs. No one makes a warmer boot. Except when they get wet. I've been told to spray them with a weather protectant at least once a month. Mine leak and it drives me crazy. Try to find something comfortable and dry and warm. I looked on www.piperlime.com (one of my favorite shoe/bag sites) and found a cute silver quilted below the knee boot with a fur trim. Not super warm, not 100% water resistant but I feel like I'm not an 80 year old woman in them or a grizzley guy. Another option is a lined rubber boot. Tons of cute ones out there.
Don't despair fellow crabby winterites! We will prevail! We will look cute, stay warm and be dry.