Riding in the winter can be great -- but having the right clothing is very important. As much of a Retrogrouch as I am, and as much as I love classic wool jerseys, the fact is that I happily embrace modern "technical" clothing materials when temperatures get into the 30s or lower.
Allow me to share some of the clothing I've been using for my cold-weather commuting. You'll probably notice that most of it comes from Pearl Izumi. That's partly because my favorite local bike shop (CC) mostly carries PI clothing and I like to support them whenever I can (the bike shop, that is), but also my experience with PI's clothing has been very good. I actually wrote some full-length reviews of a couple of these products for the bike shop's blog, and I'll include a link in those instances.
full review at CC blog)
full review at CC blog)
Pearl Izumi AmFib Neoprene Shoe Covers: There are a lot of different types and brands of shoe covers available, and I've used a few of them. But these ones from PI seem to be holding up well and are working about the best for me. With a full-length zipper up the entire back and with a fairly generous cut and shape, these fit over most of the cycling shoes I have, including my traditional-styled touring shoes (which have some fairly thick soles). There is also a MTB version that should fit over shoes with big knobby soles. These have 3mm neoprene for warmth, plus an insulated (not neoprene) ankle. They come up high enough to cover my ankles well and minimize exposure. There are also holes in the sole to accommodate pedal cleats. With well-insulated wool socks inside my shoes, and with these shoe covers on the outside, I manage to keep my feet warm down to around 30 degrees.
Giro "Proof" Winter Gloves (with liners): Giro says their Proof winter gloves are good for "near-freezing" rides, but I've found them to work pretty well even a little below freezing. These are a 2-glove set -- that is, there is a thin liner glove, with a thicker thinsulate-insulated weather-proof glove to go over them. Mine are actually slightly different than the ones that are available now (shown right), as they've been re-designed a little since I purchased mine. But on the whole, they don't seem that different, and the overall specs seem to be about the same. Giro claims the newer version is even more waterproof than the previous version. One thing I like about the 2-glove concept is that if I need to get into my saddlebags to find something, or get something out of my pockets, I can remove the outer glove (for a bit more dexterity), but keep the inner glove on so my hands still stay warm. These have large cuffs that are nice in that they'll cover jacket cuffs easily. Something worth noting is that the Giro gloves seem to fit much smaller than their listed size -- so I recommend buying them in person from your local bike shop so you can try them on. For instance, I normally wear medium gloves, but in the Giros, I ended up with XL. Go figure.
Well, those are some of the items I've been using to help me get through cold winter rides comfortably. I do have some other clothing pieces -- different kinds and brands, etc. -- but all of these are the ones I go to again and again because I like them and they work well for me. My experiences with all of them have been good and I'd buy them again -- and in the case of the jerseys, I liked them enough that I've bought several.