The key to cold weather riding is to dress in layers. Your winter cycling wardrobe should include:
Shoe covers also known as booties. Shoe covers come in various weights/thickness and block the wind in cooler temps. In really cold weather you can add toe warmers attaching them to the top of your shoe inside the bootie. This will help to keep your feet warm in weather in the 20’s and 30’s.
Wool socks in cooler temps calf length works best. Wool socks wick moisture and keep your feet warmer than a cotton sock or polyester blend.
Knickers, knee warmers, or leg warmers for rides in the 50’s and 60’s.
Lightweight tights over shorts or knickers, the combination of knickers and tights will give your knees added warmth for weather in the 30’s.
Lined tights (with polar fleece) with a windbreak front are good for the colder temps of low 30’s into the 20’s.
Under layers: Look for poly-pro, under armour, merino wool or smart wool, they are breathable wicking away moisture while keeping you warm. You can get these in both short and long sleeve tops. I would recommend a long sleeved with turtleneck and zipper in the front. With a zipper you can regulate your body temperature while riding.
Arm warmers: They are an option in combination with a short sleeve jersey. Look for a heavier weight in combination with a heavy weight short sleeve jersey as an option in place of a long sleeve jersey.
Long sleeve jersey: Jerseys come in different weights. For colder temps combination of a long sleeve under layer with light weight long sleeve jersey for temps in the 40’s. Go to a heavy weight long sleeve jersey with fleece inside in combination with under layer and you can ride in colder temps 20’s – 30’s.
Vests: A vest is a great windbreak for your core. A vest can have a mesh back for more breathability or full back for added warmth.
Windbreakers: A light windbreaker can keep cool breezes out on a windy day, while a heavier windbreaker that is also water resistant works well on colder days in the 20’s-30’s. It will also protect you from that surprise shower.
Gloves: For temps in the 40’s you can either wear cross country ski gloves or a glove liner over your fingerless cycling gloves, depending on the wind. Colder temps the options are ski gloves or lobster gloves that are like a mitten split into two compartments for 2 fingers each and a thumb. In really cold temps in the 20’s you can add a hand warmer to the top of your hand inside your glove.
Hats and headbands: Depending on how much heat you generate during a ride, and how much hair you have will depend on what you wear on your head under your helmet. In the 40’s you can go with a headband that covers your ears, but if it’s windy you may want a light weight skull cap. For temps in the 30’s go with a wool cap that covers your ears or a balaclava. The balaclava will protect your head, neck and nose and mouth. Having your mouth covered helps breathing because you are warming the air as you breath.
When buying clothing remember jerseys and tights come in different weights. Make sure you know what you are buying.
You will have to determine what layers work for you. Depending on how fast you ride and how much heat you generate. The key is not to over dress.
Check the weather before you ride. If the sun is out even in the winter it will warm up your ride, some. Check the wind speed and direction and try to plan your ride with a tail wind on the return if possible. Usually on the seacoast a northeast wind coming off the water will be colder than a southwest wind off shore.
No such thing as bad weather only bad clothing. So remember to check weights of clothing and layer and enjoy some winter cycling. As long as the roads are clear a winter ride can be a joy in the crisp clear air. And along the shore you may even catch sight of a snowy owl here for the winter.