Tip Number One
Protect your feet! My feet are so sensitive to the cold weather, so it's always important that I protect them. Make sure to wear shoes with the least amount of mesh. Hold onto those mesh ones for the summer months. Having more leather and less mesh help when it snows outside to keep your feet dry. I tend to wear two pairs of socks when running in the winter to both keep my feet warm and to keep them dry, so feel free to do so too.
(Photo from here) Tip Number Two
Dress appropriately. It's a little tricky to dress for winter running since you will probably still sweat even if it's thirty degrees outside. A little tip I learned is to dress like it's twenty degrees warmer outside. Yes, you will be a little chilly when you start, but you will warm up very quickly. Wear layers, but make sure they are light. Also, don't leave the house without a hat and gloves. These parts of your body are very sensitive to the cold weather and are often neglected. Make sure the fabric will keep your hands warm but still a little bit breathable.
Tip Number Three
Wear bright colors. Since we have less sunlight in the winter months, it's likely that you will be running in the dark. If this is the case, stick to neons and bright colors. Make sure at least either your running tights or your jacket is a bright color. Pull out those crazy bright running shoes you haven't warn in years, and just make sure people can see you for your own safety.
(Photo from here) Tip Number Four
Warm up before you head out. Since you probably want to spend as little time as possible out in the cold, start your warm up at home. Do some jumping jacks or sprint up and down your stairs. Not only will it prep you for your run, but it is much easer to attack the cold weather when you are already warmed up.
Tip Number Five
Strip off your running clothes immediately. As soon as you stop running, your temperature will begin to drop. Pull off your wet and/or cold clothes, take a hot shower, and pull on something warm and comfortable as soon as you can. This will prevent your body temperature from dropping too much, and you will be so much more comfortable.
Keep it up with your winter outside running! You're a rock star.
Cover photo from here.