Brighter than God: the Light Motion combo of the Seca 1700 Race and the Stella 300. It's the ultimate night riding set up for the darker months. The lights are compact and both the lights and the batteries are easy to mount to bike or helmet.
The Bellweather Convertible Jacket: weather resistant with a wind flap inside the zipper, a snug fit, and removable sleeves for those times when a jacket is too much, but the jersey isn't quite enough.
Dakine White Knuckle Gloves are perfect for when it gets just cold enough that you really, really want something more than the Royal Mercury gloves. The key is the 100 grams of Thinsulate insulation.
Cold, wet, and windy? The Royal Mercury makes a great riding glove for temperatures ranging from 40F to 48F (5C to 9C), particularly when the wind is blowing. The water resistant/windproof back is just enough, while the silicon grippers on the palms and the fingers keep your hands secure on the brakes and bars, no matter how sloppy out it is.
Definitely a pack for wet weather! The rain fly works well, and the pack itself is capable of swallowing as much gear as you are willing to carry. The magnetic clip on the sternum strap keeps the hose exactly where you want it.
What makes the Raceface Ambush so good is the custom fit and being able to put on and remove the pad without removing one's shoes: key in winter weather.
The Royal Signature Short: this has quickly become "the" short for me. They breath well, they have a bomber beltline fastener with snaps and a clip, waist tab adjusters for a custom fit, are water resistant, yet breathable at the same time. Plus--knock on wood--they have as yet to hook my saddle in technical terrain or on steep trails.