This becomes increasingly important as the temperature falls. Why? Wind chill.
The wind-chill effect is why air feels colder than the actual temperature. Here's an example. If it's 50 degrees and calm, it feels like, well, 50 degrees. But if it's 50 degrees and a 15-mph wind is blowing, wind-chill charts tell us that it feels like 36 degrees. Big difference.
Now let's say you're riding into that 15-mph wind at 15 mph. This produces a 30-mph headwind and an effective temperature of 28 degrees. Brrrr!
So, be smart and face the icy blast when you're fresh and dry. Go into the wind for the first half of the ride. Then when you're getting tired and damp, you can turn and let it blow you back home. Suddenly it'll feel a lot warmer.
The colder it is, the more essential this tactic. On a 30-degree day, the windchill created by riding into a 15-mph headwind is a frigid 2 below zero. Holy frostbite! If you encounter that kind of cold after you've worked up a sweat, they'll be undressing you with an ice pick.
Remember, even on a calm day the speed of cycling creates wind chill. Make sure your jacket has a full-length zipper that you can run up and down to control airflow and limit sweating.