This is one of my favorite questions and topics EVER. I have ridden through many a cold winter, and I would like to think I have whittled down my clothing choices by now.

Rule number one -- no cotton. Remember, wet cotton (from sweat or elements) sticks to your skin much, MUCH longer than polyester or blends.

Rule number two -- try to go with merino wool as much as possible. Yes, it's more expensive but, in the long run, will prove more reliable, long-lasting, and comfortable. Try sales in September-October-November at your local Marshalls or TJ Maxx. They will have brand-name merino sweaters, for instance for about 20-40 bucks -- last year's models/styles basically that originally were prices at 80+ dollars. I bought about 6 different ones there in the last couple of years that proved very good in the winter -- super warm, THIN, and you can even wash them by hand in the sink and then lay them flat to dry (I sometimes even buy them size up to allow for shrinkage).

Also, at these discount store you should look for winter gloves at dirt-cheap prices. I happened upon a pair of HEAD winter gloves that I absolutely LOVE. Here, you will play a game of trial and error where two seemingly similar gloves will have drastic differences in how they keep your hands warm.

I have worn these HEADs in temps down to -15 F with wind chill with no liner gloves, and my fingers NEVER felt numb due to cold. I don't know what it is (they have thick fingers but not much more than other brands/styles).

Another thing -- good shoes/boots I REALLY like Keen Winter boots. They are not heavy to pedal in, they sustain temps below 0 F, and they have low maintenance.

MY other favorite brands are Icebreaker and GoreBikeWear. I only like to buy them on Amazon or at discount places, not directly from their online sites.

Gorebikewear is one of very few brands that does, in fact, make fast-drying, moisture-control, light, well-made, long-lasting, really rain and snow-proof clothes (like jackets and pants).

Yes, I actually miss riding in snow or winter rain right now when it is close to 80-100 outside because I am not wearing these clothes. Kind of crazy thinking, and I know I will have my time for this (in about 5-6 months) so I should enjoy my summer clothes. Oh well.