Jackie/Viva, in our family everyone has either a tiny head (me and mom) or a ginormous head (my siblings and father). My mom and I can fit children's glasses and most hats slide down over our ears. We refer to it as being either a pin head or a pail head. My fiance has a pail head.
As to winter, fleece lined tights are a good option. I bought some at amazon last year and they were very cozy.
I have four or five down filled jackets that range from hip length to knee length.
Kiehls ultimate hand cream is a dream. My hands look prehistoric and today is the first day that is was below 0C. As it gets colder, they will crack and bleed from the cold dry air. This hand cream is a life-saver.
Coconut oil - I add a glob into the tub in the evening or my legs are like a snake shedding its skin.
Heated seats are a given and an attached garage helps too. If you are truly cold averse, heated indoor parking at the office. And last but not least, a month in a tropical climate preferably all of January. My widget tells me I leave for Mexico in 66 days. I will be there for 5.5 weeks. Ahhhh
ETA: I thought of one more. Gehwol foot cream. There is a regular one for daily use to keep heels in shape and a special one for cracked heels if you forget the regular one. Life savers!!