|From Worthless Garbage|
The head region does more to regulate body temperature than any other area of the body. Getting the hat situation figured out is more important than a jacket, as important as a morning bowl of cereal.
On chilly days 40-20F I were the black hat of the right. Its a loosely knit viking cap that breathes nicely and works great on days I have to go pillaging. The sunglasses (natives) are enough to keep my eyeballs happy down to about 10F. However, they don't do a damn thing when the snow starts falling.
The red hat is a pollypoo blend of some sort. It does not let nearly as much wind in as the viking cap, and is much tighter. It keeps my head toasty enough in the negative Fahrenheit temperatures (-5F has been the coldest we've had this year in lovely Picksburgh.) I feel a little self conscious about wearing a red hat under a lime green helmet, but I really don't want to buy another hat. When the sky starts falling, there is no substitute for ski goggles. I really don't like to wear them because they're a pain with my helmet, but sometimes there is just no choice.
On the subject of helmets, I've had my Giro for something like 6 years and its sooo nice. I just love it to death. I don't have to much trouble getting a hat under it.
The final piece of head gear I swathe myself in in the cold is a neck warmer. It makes a huge difference in holding in body heat. At this point in the winter, when I'm used to the temperature, I can wear the warmer instead of a jacket. It makes that much difference.