My Father In Law gave me a Chicago style hat which I've nearly worn out.

Looks like a British sports car driver's cap ("Grand dad cap") but it has earflaps that can be brought down to cover ears and more of the back of the head. The flaps are tucked up inside when not needed.

My parka also has an insulated hood and I carry a neck fleece for those really cold days.

What kind of hat(s) do you wear in cold weather?

For the most part I wear a Tilley Winter Hat (wool with brim). I wear glasses, and when it snows I HATE getting my glasses wet, thus the brim is important to me.

I also wear a Carhartt knit cap when needing to keep ears warm over a longer time.

I bought a Kromer Rancher Cap last year (like their famous Kromer Stormy Cap, but the Rancher has more insulation and bigger ear flaps) BUT I have a giant head and even the largest size available is a bit too tight. I bought a wooden had stretcher and need to wet down the cap and try stretching it a bit. I hope it works.