Forget the standard advice. I am a ten-time marathoner. Believe someone who's done cold-weather running (and who recently ran a personal-best marathon on a 30 degree wind chill day).
Here are the tips.
(1). Do morning runs. The sun is strongest, and the skies often the clearest, at or around sunrise. The winds often are the calmest as well, as the sun has yet to get the atmosphere "cooking" and causing the air to move around. This means you'll feel the least uncomfortable if you time your runs in the 6am-8am range. This holds true even if the air temperature is five to ten degrees warmer in the late afternoon. In my experience, it gets nasty after 1pm as it often gets cloudier and windier after four or five hours of sunlight. The sun also loses its warming strength once it is past its peak position. Remember, until daylight savings time moves the clocks ahead an hour in early March, the sun is actually at its highest point in the sky at or shortly before noon!
(2). Watch for ice. Another reason to do morning runs is that the sun has yet to melt any snowpack (even if the air temperature is well under 32 degrees Fahrenheit). Melting snow will turn into ice quickly, especially when the ground surface has a hard freeze from prolonged periods below freezing.
(3). Hydrate but never drink anything cold. I actually don't like cold drinks at any time of the year. Hot drinks are overrated and your key should be quenching your thirst. The cold weather will tend to dehydrate you by sparking an urge to urinate. The reason: the air in the winter is often very, very dry. The best measure of this is not the humidity but rather the dewpoint (temperature at which water vapor in the air will condense on surfaces). The dewpoint in the winter is routinely below zero.
(4). Cover your head and face. Most body heat is lost there.
(5). Minimize all exposed skin. A no-brainer. Your legs can be exposed, but use an oil-based lubricating jelly to keep moisture and avoid serious drying out of your skin.
(6). Don't overdress. You do not need five layers of clothing; a garbage bag is a great way to warm up as well as a fantastic conversation starter. Wicking clothing is a must but you need only one thin undergarment underneath it.
(7). Mittens not gloves. Your fingers will get cold in conventional runners' gloves. Buy hockey gloves (seriously!). The Canadians know something about fighting the cold. So don't be a dumb American! And ball your hands into fists so your fingers stay warm together.
(8) Take care of your other extremity. Your extremities will be most prone to frostbite. But men must not forget about your other extremity, the one which is the only one you have. This is an issue for any long run taking you outside for an hour or longer and especially if you are running at an easy pace to put in mileage (as opposed to a brisk tempo run at race pace, which has the added protection of generating much more internal heat that may counter the temperature/cold moisture problem). Perspiration will chill and start to freeze on your skin if it isn't wicked away. If there is any place to have several layers on, it is the waist area. Try three layers (sweatpants over shorts, for example). This is one area to monitor during your runs regardless of whether you feel anything.
Eric Dixon LLC