1. Tuck Everything In to Everything Else
For the real, real cold, tucking your shirt into your tights/pants is your best defense against the cold – but don't stop there! Make sure the tops of your socks reach the bottom of your tights and that your MITTENS (see below) reach your shirt. For an extra way to defy winter, wear your watch over your shirt. Seriously.
2. Leave the GPS at Home
Just concede to the fact that you're not going to be breaking any speed records on this run and go by effort, not pace. It's a lot harder to run with 18 pounds of extra layers and side stepping ice patches while simultaneously hurdling snowbanks. And let's face it: you've worn your GPS for this route 84 times and recorded it to the hundredth of a mile each time. It hasn't changed, I promise.
3. Mittens. Not Gloves. Mittens
If your someone who's hands get painfully cold while running, my number one rule of cold weather running is mittens. Think about it, your body (and fingers) generate heat ... why would you separate them in little tubes to like the heat dissipate into winter instead of radiating into other fingers? For the ultimate solution - wool socks are just like mittens, but your thumb is invited to the warming party (sure, you'll have trouble with doorknobs ... but we all need to make sacrifices).
Keeping warm is keeping dry. This means that making sure your base layer is a wicking material that takes sweat out and away from your body. Cotton gets soggy and can send you straight into the perils of cold if you don't ... (see next bullet)
5. Choose your Direction Wisely
We've all been there. Running along, feeling FANTASTIC, starting to warm up and sweat, when you reach the halfway point only to turn around and be hit in the face with the wind of a small tornado. Your pace instantly declines, your eye lashes freeze, and that sweat you worked up earlier comes back to chill you to the bone, and you're five miles from home. If at all possible, run into the wind first, not only will you feel warmer throughout, you can also negative split!
6. Invoke a "No Complaining" Rule
If you're running with a group, the following should be understood at all times.
Yes, it's cold.
Yes, I too wish it were summer.
Yes, complaining about it just makes it seem worse.
However! Running with a group is not only safer, the mutual, unspoken suffering makes it better.