What would be the first piece of advice?  Don't sweat.  Sweating cannot be avoided because you are exercising and you want a workout.  If you do not sweat you do not hope for improvement.  In the colder temperatures the sweating needs to be managed better than when it is hot.  Let's consider some aspects of sweating.

Why do you sweat? It is your way your body cools itself down when it gets too hot.  Your body will get too hot based on the clothing you are wearing.  You know that your body will heat up with exercise.  There are rules of thumb that may guide you: dress like it is 15 degrees warmer than the outside temperature, when you start riding you should feel cold.

Learn what helps you feel comfortable.  The extremities need your attention.  Hat for your head. Gloves for your hands and socks plus shoes.  Each body reacts differently.

The wicking capability of the material on your head cover is so important.  I tried a stocking cap first and it was too hot. I picked up a cycling specific cap that also covers my ears and that  worked much better. This item also noted that it was wind resistant.  I do not like the feel of wind penetrating my layers and reaching my skin.  There are a variety of winter cycling items to consider and it is good to read the reviews.  

How long will you be out on the ride?  When I was riding in temperatures of 20 and 30s my feet and hands would start to get cold after about an hour when using my standard shoes and  gloves. Another thing to consider is whether there is snow or rain. I will sometimes pack an extra pair of gloves and hat. 

This was on one of my first cold weather rides and the rain shell was plastic.  As you might imagine, this jacket did not let out my perspiration and the layers got soaked.  You learn by trial and error.   I decided to get a rain jacket that had a breathable air transfer. This new jacket was wind resistant to 60 mph and waterproof for the rain.  The pit zippers help to regulate the inside  temperature. I very much appreciate the wind resistance. 

I found that the jacket worked well with temperatures from 60 down to single digits. The membrane is water repellent and windproof. The jacket has a two-way zipper that works to open the front and there are armpit zips.  I keep the armpit zips open all the time.  The only time I close them is on terribly cold and windy days.  These zippers allow the free flow of air to maintain a dry environment.

The fleece buff is something that I really find comforting.  I find that an exposed neck in the cold really adds to my discomfort.  This model easily covers my ears.  I need the neck gaiter to cover my mouth and warm the air that I breathe. I can easily pull it up to also cover the nose.

I am usually comfortable with just basic full fingered gloves.  I will also bring a pair of heavier gloves to warm my cold hands. I also found a pair of hunting gloves that worked great and they are orange for visibility.

What suggestions do you have? Enjoy your winter rides.

Convenience is my top factor. I like to choose a route that I can take from my house. When I have the time to mount the bike on the car rack and drive to a spot that is a treat.  

How much time do I have? You may have your bike with you and you can ride between work  and  home.  I know that some of you are commuters and your ride is part of getting home.

Safety is a big factor.  How do I feel about car traffic along the route? I prefer to ride on less traveled roads.

Am I excited about my proposed route? I think about where I will ride in advance of departure. Under this factor and several aspects.  Many of us have multiple bikes: mountain, gravel, fat tire, road, etc.  For example if my last ride was on the road, I probably will want to do gravel today.  What is my focus or goal for the ride? I want to set up anticipation and excitement about going outside. What am I looking forward to see along the route?  I like to take photos on the ride.

Will you ride with someone? I will ride by myself almost 100% of the time. I know that with a riding buddy, this becomes a major factor.  

Sunset is earlier in November and darkness comes much faster than in the  summer. Right now I am enjoying the residential rides close to home.  I can get out quickly and I am close to home to beat the dark. I also have options to keep moving and not get slowed down by late afternoon traffic.  I am familiar with various routes and can quickly make adjustments during the ride.  I can create a route that allows 20-30 miles of riding.

I am lucky that within 3/4 mile I can get to a network of gravel roads. Those rides could go for a long time.

What factors influence your ride choices.?