Cycling generates a lot of heat so clothes that are warm and comfortable have to control the buildup of heat and moisture as well as insulate and protect from wind.
Your particular metabolism, physical condition and riding style will determine what's needed to keep you warm. We see people who ride in Carhartts and bunny boots and others who ride in lightweight ski gear. You'll have to experiment.
Your outer layer on top and bottom should have a windproof front and breathable sides and rear.
Goretex and other "breathable" waterproof materials become clogged with ice at below-freezing temperatures. As windproof front materials these fabrics are acceptable but unnecessarily expensive. On the sides and back of your riding clothes they'll trap moisture and freeze you.
Layer various weights of polypro, capilene, drilete or thermax under your outer, breathable/windproof clothes. Multiple light layers with neck zippers let you adjust your ventilation as you ride.
Your base layer (against your skin) and mid-layers should be synthetics or wool. Cotton in these layers will feel wetter and colder than the above materials. No T-shirts!
Over the years, the Kucharik company has most consistently offered clothes that meet our need for outer layers with windproof fronts and very breathable sides and back.
Windproof jocks, as used by skiers, are much appreciated by men. In an emergency, stuff a mitten or hat in your pants.
If you feel warm as you start out then you're probably overdressed for any ride longer than a half hour.
Kinneys' snow jogger boots are light, warm and inexpensive. They can be adapted to use SPD or Grafton cleats. Try them on with at least two pairs of heavy socks. If Kinneys doesn't have them this year,Big Rays, LL Bean, REI and Eddy Bauer have similar shoes. For extreme cold or sensitive feet try Sorels or neoprene boot covers.
Power grips are a type of oversized toestrap used in place of toeclips. They work well summer or winter and they're available in an extra-long version for winter footgear. Because they're made of fabric and don't compress your toes, they're warmer than toeclips.
Bike pogies are oversized mittens that fit over the handlebars. They let you ride barehanded when you'd wear gloves and let you wear gloves when you'd need heavy mittens. This improves your control of the bike and makes eating, drinking, clothes adjusting and nose wiping easier.
Disposable heat packs can be part of your normal system or can be carried for emergencies. They come in hand and foot varieties and last for 2-5 hours, depending on conditions. The reusable types are heavy and bulky and less effective.
Carry headband, hat and facemask and try them in different combinations. Neck gaitors and balaclavas are variations on the theme you may find useful Your face, head and neck will need different amounts of protection as conditions vary. Uncovering your head is usually the simplest way to dump heat.
You may need to change the sizing pads in your helmet or remove them entirely to fit your winter headgear. Some hats are made specifically to fit under helmets. Try taping over the vents in your helmet if your head gets too cold.
If you're riding in a headwind or falling snow you'll find eye protection very helpful.
So true!!!