[herr_oberst]

I don't like a headband for cold wet weather. A polypro skull cap, or a wool beanie (or a skull cap and a cycling cap.). Wool neck gaitor. I wear glasses, so that's my eye protection. Warm gloves, warm socks and shoe covers.
Three or four thin layers for upper body (base, L/S jersey and goretex jacket, sometimes a vest thrown in. All fit very close to my body. I don't like flappy clothing when I ride. I haven't found the perfect garments for my legs, but I know I hate nylon rain pants more than I hate wet legs, so I usually just use my heavyweight, lined Descente tights under my 3/4 length cycling shorts.

Also make sure you eat and drink. Your body is trying hard to keep warm and you need extra calories and water. It's hard to do when it's cold. I'll put a water bottle in my jersey pocket under my rain jacket to try and keep it a little warmer.

Edit. This is Oregon cold, not Canada cold. So, this information might all be useless to a stud like you cycling up in the great white north.