Less Is More
Keep a log and track the apparel combinations that work for you. This way when next year rolls around, you'll have a go-to resource to help you decide the best options. Dress for temperatures that are around 15 to 20 degrees warmer than the current temperature (including wind chill) to account for the rise in body temperature once you begin to exercise.
Run Against the Wind
I'll never forget my final 20-mile training run for the Goofy Challenge. I ran an out and back course along Chicago's lakefront path. I guessed wrong on the wind and ran with it for the first 10 miles. By the time I got to the turn around point, I was already overheated and sweating.
It was a long, brutally-cold run back into a strong headwind, and my sweat made things even colder. Listen to the weather before your run and determine which direction the wind is blowing. Try to plot your course into the wind on your way out so you can enjoy a nice tailwind, and stay warm, later in the run.
Warm it Up
The hardest part of winter running can be getting out the door, especially on cold, dark mornings. To get you in the mood, take a hot shower to pre-warm your muscles and wake up. Performing five minutes of dynamic warm up exercises in the house pre-run is also an effective way to both warm up and prepare your body for the run ahead. Allow yourself more time to warm up outside to. By running easy for a longer period of time at the onset of your workout, you'll prevent injury and be less likely to go too hard on cold muscles.
Stay Low and Relax
When the roads are slick, snowy and icy, consider wearing YakTrax. They slip over your shoes easily and work like chains on car tires to provide better traction and reduce the risk of slipping and falling.
Focus on relaxing your form too, as running "tight" because you're cold can cause a muscle strain in your hips, groin or inner thigh muscles. Shorten your stride and keep your feet low to the ground. You'll run more efficiently and reduce the risk of injury. When running on snow, choose fresh or packed snow for better traction.