The base layer is essential. Something like this little number from Pearl Izumi works well in the winter. It will help keep your core warm by trapping heat and wicking moisture away from your skin. It’s the first thing you put on (after your heart rate monitor) and it should fit snugly. From there you can put on your additional layers – maybe a long-sleeve jersey and a soft-shell jacket, depending on the weather conditions.
Choosing the right options for the specific weather conditions of the day is a bit of art and science, and can only be fine-tuned through personal experience. It takes time to develop, so pay careful attention to what your wearing, how your feeling, and the precise weather conditions of your rides. Always dress in layers so that you have some flexibility to adjust out on the road, and pay attention to how those adjustments work for you.
You want to be a bit cold when you start your ride as you’ll warm up soon after you start pedaling. If you can stand outside for 10 minutes without riding and you’re still nice and warm, you’re overdressed and you’ll be uncomfortable out on the road (sweaty, then freezing as you remove layers).
If you pay attention and experiment with different options you’ll develop your own personal strategies to help make your rides more comfortable in a wide variety of conditions. A couple of options that work well for me are my cycling vest and arm warmers. I find these little additions can really help on colder days – the vest because it blocks the wind and the arm warmers because they fit tighter than a long-sleeve jersey. The one item that is included for every ride, however, is the base layer.
Of course, I’ve only talked about the core here. There are many more items to consider for cold weather rides (gloves, head gear, tights, shoe covers, etc.), but I’ll leave those for a future post.