Every morning I get up about 50 minutes before I run to drink coffee, watch ESPN, do stuff, and most importantly watch the weather. It's usually not enough to watch it once I have to see it twice. From there I figure out what I'm going to wear.
Mittens below 20F and gloves 20F to 50F.
Dress socks and cotton socks below 10F.
Two head caps below 0F, one of which I can pull over my neck if too windy.
Heavy head cap 0F to 25F and a thin one 25F to 40F.
Shorts 30F and above.
Thin running pants 15F to 30F.
Heavy running pants 0F to 15F.
Thin and heavy pants if wind chill is 0F and below on real windy days.
Fleet Farm top 40F+.
Fleet Farm top and pull over 25F to 40F.
Fleet Farm top, long sleeve shirt, and pull over top 10F to 25F.
Fleet Farm top, pull over and heavy vest -5F to 10F.
Fleet Farm top, sweat shirt, and heavy vest for really wind wind chill days below -5F. Maybe toss in a wind breaker if wind chills below -25F.
The wind can alter these, but normally they have to be over 15-20 mph winds and I'm exposed a lot.
It has been an easy winter to run in. I can't wait to the trails are ready to go. I love the road, but the trail runs are more forgiving and necessary if you plan on doing and ultra on them.