I have run almost everyday in the UK which obviously includes eight winters. Over this time I learnt a few things about running in these conditions which I thought I would share with you. They're not extraordinary and you probably know them but here it goes.
Check the weather the night before and put the clothes out you'll need for the morning. If it's going to rain make sure you know where the petroleum jelly aka vaseline, is to prevent chaffing.
I find that you don't need gloves if the temperature is 10 *c or over.
Always expect it to be raining. Wearing a cap with a peak keeps the rain off your face and feels better.
Listen to Running podcasts.
Keep wrists warm with wrist bands.
Jackets are overrated. They keep you warm for the first mile and then you'll overheat and sweat. If it's raining you don't need a jacket because rain means it's warm. Only wear a jacket if it's cold enough to be snowing or sleeting. Sounds harsh but honesty it's true.
Wear mittens, not gloves, mittens isolate each finger and then they get cold.
Wear a buff (headband) because a hat will make your head overheat. Also a buff is excellent for keeping earbuds in for your music.
I wear yellow tinted glasses, this keeps the cold airs from your eyes and makes for slightly better night vision from car headlights. Not a necessity.
Don't bother too much with lights etc, controversial I know but from all my experience of running mostly on A roads and pavements in the dark drivers don't see you whatever you wear. Face the traffic. Stick to routes with pavements and street lights if possible. Don't be too stubborn to stop and jump into the grass verge when you think a car hasn't seen you. On really dark lanes without pavements, in the dark, remove your ear buds, earphone etc.
Above all remember that it isn't so bad once you're out there.
Anything Else? put it in the comments.