I think there is a lot of experimentation when it comes to settling on winter/cold weather gear, as every person's sensitivity to cold is different, the humidty/wind combo, and how long your rides are. I still have not found the perfect gear for myself, the main issue being my hands. A couple of observations from me:
  • Glasses: Glasses with removable lenses are a great investment. I recently bought clear photochromic lenses for mine (they darken with light) and I could not be happier. Why did I not invest in them 5 years ago?
  • Shoes: Since you are in the NW, rain may be a persistent issue. Coupled with lower temperatures, a pair of waterproof cycling boots might be in order. [Personally, this is where I am shy at the trigger... I look and look, but cannot decide].
  • Shoe covers: for me, they do not work well. In 40 degree weather, I can go for 1.5 hours with shoe covers, but my toes start getting cold. 2 hours or more has resulted in numb feet. Not fun.
  • Knee warmers -- I cannot stand them. I prefer a good pair of knickers. My rule for covering my knees during rides (based on a couple of readings) is to cover the knees in any temperature below 65 degrees. There is not much blood flow to the tendons in the knee area, so I prefer to be on safe side and keep my knees warm. My knees never overheat.
  • Arm warmers I use every now and then, when the temperatures are in the 50s (Craft short sleeve 'extreme' baselayer, short sleeve jersey, arm warmers, knicker, wool socks). It's nice to be able to remove them during a ride, if needed.
  • Pants: when the temperature drops to 40 or below, windproof tights are nice. You can put some nice tights over your cycling shorts. If you have to wear rain pants, the tights can be lighter.
  • Underlayers: I love Craft warm and windproof underlayers
  • Rain jacket: Showers Pass has some very nice ones.
  • Head cover: get a beanie that covers your ears and a balaclava for colder days. Together with happy knees, ears that are not frozen will keep you happier. Re the balaclava, I learned last winter (riding in dry temps between 30 and 40) that the same gear goes a longer way in terms of warmth when you add the balaclava, which covers your neck and chin. No exaggeration: even my toes felt warmer when I used the balaclava.