Layering applies here too. On your head wear a windproof skullcap. If it's colder or rainy, add a helmet cover. Cyclists in very cold areas have winter helmets with the vents covered with reflective tape. In my seat bag I have a motel shower cap as an emergency helmet cover a thin polypro balaclava, which I can use as a wicking layer and if necessary pull down over my face.
For your hands winter cycling gloves are a good start; however, they may not be warm enough. Get a pair of lobster shells, which have the index and second finger together and then the ring and little finger. These provide more protection and still allow you to manipulate your shifting and brakes.
I carry polypro glove liners in my seat bag, which I can wear as a wicking layer under gloves and shells for added warmth. If I need to remove the outer layers to get food out and unwrap it, for example, the glove liners provide some insulation.
You can also wear layers on your feet. Start with thicker socks. I like wool socks that come up my calves. Loosen your shoes so that you have good circulation in your feet.
If your feet are still cold wear booties; however, get booties designed for winter riding, not tight racing booties. As a cheap alternative get a pair of large heavy wool socks, cut holes in them for your cleats and wear them over your shoes. Or in a pinch wear plastic bags over your socks, taped closed at the top.
Stop and Adjust
In the summer being a little too hot or too cold while riding is unpleasant; however, in the winter wearing too much or too little may have serious consequences. Always carry an extra layer for your torso as well as your head and hands. If you start to chill, stop and add protection. If you start to overheat, stop and adjust your layers so that you don't get sweaty.
If you don't take the offseason literally and continue to ride, you'll have good baseline conditioning when you start training for your main cycling season. By riding outdoors you'll have more fun than grinding away on the trainer. If you dress in layers, wear base layers that wick away perspiration and adjust your clothing as the conditions change, you can ride comfortably in most conditions. Follow these tips and, like me, you'll enjoy riding outdoors year-round.Search for a cycling event.