Anytime the temperature hits 39℉ I feel you can call it Cold Weather Riding. Since the start of December this has been our riding reality pretty much every ride. Even if there are parts of the ride in the 40’s at least the start and/or the end of the ride have qualified for Cold Weather Riding.
Cold Weather Riding is just like Warm and Hot Weather Riding except that you are cold. The key to not getting cold is to stay warm which is done by layering up your clothing. Typically when I ride I wear socks, shorts, short sleeve jersey, fingerless gloves, headband (for sweat), helmet, and sunglasses. Layering up for Cold Weather Riding means starting there and adding more.
When it is 39℉ or colder I generally have all of my riding clothing on which means I can ride in temperatures as low as 8℉. Any lower than that and I should consider walking, driving, or staying indoors. All of my gear means thick socks, shoe covers, tights, long sleeve jersey, heavy riding jacket, lobster gloves, neck gator, and helmet cap.
The main issue I run into with all of that on is getting too hot. The problem with getting too hot is that you sweat and then that sweat can turn into ice. Once your clothing starts to ice up you can get into big trouble with frost bite and hypothermia really quickly.
This is why you want to build up your clothing in thin layers. Then as you heat up you can stop and remove a layer and then continue on. If you start getting cold again you can put those layers back on.
Personally I have found that if I feel a little cold as I start a ride then I will be fine. As I ride my body will heat up from the activity of pedaling my bike. If I am comfy or warm when I leave then I am going to be too hot pretty quickly and will start considering what to take off and when. If I am too cold when I start then I think about what I might want to add. And, yes it is as accurate as the story of Goldilocks.
For gloves I mentioned “lobster gloves” and I am guessing you aren’t sure what I am referring to here. If you have been cycling in cold weather you may have seen other cyclists wearing gloves with fewer than 4 fingers. These people have either lost some of their fingers or are wearing lobster style gloves. The originals, as far as I am aware, are the Pearl Izumi Lobster Gloves™. They combine the idea of a mitten with some functionality of a glove. I prefer the Planet Bike Borialis cause the name is better, the company is better, and the glove is better:
These gloves have allowed me to ride comfortably in Cold Weather Riding and still have total control of the bike. They are pretty much ski gloves but the combined pinky and ring fingers make them even warmer.
For my neck gator I am a big fan of Buff ThermoNet . They are seamless so you never get chafing and they can be used in a multitude of ways. I have a lighter one that I use in the summer for a headband.
For helmet caps I recommend getting a dedicated skull cap for Cold Weather riding. Since Kate needed one too we got this 3 pack:
You dont have to spend a ton of money to do Cold Weather Riding but you do need to spend something. Frost bite and hypothermia can happen very quickly and be a real bummer for you. If you are in doubt about what to wear in your area head to your local bike shop and ask questions. They can even sell you some of the gear and give you advice on anything else. Heck leave a comment here and maybe I can help.