Cold weather riding can be a lot more enjoyable if you have a winter cycling wardrobe to keep you warm. There are a lot of cold weather pieces and it can be difficult to know what the best investments will be. We have found that it is best to buy clothing in stages, beginning with pieces for cool weather riding. Then, you can add purchases that will work in conjunction with past purchases as you layer to keep warm in colder temperatures.
50 - 65 degrees
Cool weather riding begins when temperatures drop below 65 degrees. Between 50-65 degrees, you may notice your extremities getting cold, especially if the sun is not shining. Remember that although your legs are moving while your ride, for the most part, your fingers and toes are not moving, so those are the first body parts you will notice getting cold. Long fingered gloves and toe covers will be just enough to do the job. You would be surprised how warm your toes will stay just by covering the front of your shoe with a toe cover. Additionally, it is important to keep the wind off of your chest to make breathing easier - a windproof vest if perfect for this. Combined with a pair of armwarmers, you can easily moderate your temperature as your ride progresses by shedding the vest or armwarmers and stowing them in a jersey pocket. It is always important to keep your joints warm, so cover your knees with a pair of knee covers. It is just the amount of protection from the cold and wind, but not too much that you would need to remove them should the sun start to shine.
It is in these temperatures that you will find that what you are wearing when you return from your ride may be different from when you left - especially if you head out before the sun is at its brightest. With that in mind, keep your accessories lightweight and easy to store when riding in this temperature zone.
In this temperature zone, you will usually find that you are not shedding accessories as you ride. A vest is still a very practical item, but now a baselayer and thermal jersey keep you warm under it. Some folks prefer a full windbreak jacket during these temperatures. You may find that you can wear the same lightweight gloves you have been wearing if you combine them with a glove liner. Otherwise, look into a midweight glove. Knee warmers are still appropriate, but some folks may be switching to full tights at these temperatures. Typically toe covers are still all you need, but you will probably want a cool weather sock. Remember that thicker is not always better - especially if you have a traditional snug fit in your cycling shoe. You always want enough room to comfortable wiggle your foot in order to keep circulation to your toes.
You are well into winter riding and you will need the both thermal layers as well as protection from the wind. Full booties and wool socks will help keep your feet warm, but remember to leave enough space in your shoes to wiggle your toes freely. You may find that chemical warmers in your shoes and gloves will help keep your extremities toasty.
Below 25 Degrees
Many cyclists are able to continue riding in these low temperatures by keeping in mind that while staying warm is important, so is staying dry. Remember that while you are riding, you will build up heat. Try to keep enough ventilation to keep from sweating. Once you begin to sweat, you may find that you quickly chill. Most winter jackets are equipped with vents and pockets that you can unzip to provide ventilation as needed.