Carly gave a great demonstration where she "dressed" herself in layers, gave us recommendations about how to stay warm and comfortable with layers. Carly encourages thrifting and finding cheap ways to key pieces for winter riding. I appreciated that she opened up the floor to the winter bikers in the room so we could share what works for us. Read her recap below, and add your knowledge to the comments section.
FEET - Keeping you extremities warm is a big deal. Numb toes is common when cycling, even in summer, so your feet especially will need good insulation.
Socks - Thick wool or warm tech fibers are preferred.
Boots - Look for waterproof, insulated footwear. Most cyclist prefer wide, grippy soles if they're not clipped in. If they ride with cleats, they will use a winter pair, or at the very least cover their summer shoes with the neoprene booties.
HANDS- Windproofing, insulating & retaining function of your hands is important. Usually, basic mittens or gloves will do, but there are some special considerations.
Liners- Are useful for that extra warmth. You can also carry an extra pair if yours get wet.
Lobster Gloves- Are better than mittens when it comes to dexterity, but sacrifice some warmth. They also usually have reflective bits which are a plus when riding in traffic.
Handlebar Gauntlets - Use these when you're going for the EXTREME biker look.