I hate to continue to use Blair Waldorf as an example, but she really does provide great images of womenswear.
I have always had difficulties in the winter with hats. Though very necessary, they can easily be disastrous and unattractive, like those horrid little beanie hats. This year I have decided to return to the 1920s and wear a cloche hat. Make sure you purchase one made out of wool for it to be functional as well as a beautiful addition.
If you took my previous advice and purchased a brightly colored peacoat, I suggest you stick to a darker cloche. I recently acquired a gray one similar to the one above and an adorable black one with a cream band and bow. Do not make the mistake of thinking these hats dated. They are flattering on most everyone and are the best way to keep warm in the winter! However, the style of hat is not purely for winter. Change the materials used and you have a perfect hat for your next derby or polo match.