I don't know why school track classes wear sweatpants and sweatshirts. The wind blows right through them and is very cold on bare skin. After you run for a while and get sweaty it is worse because the fabric absorbs the sweat becomes ice cold. This ice cold fabric then blows up against bare skin.
Never wear sweat pants and if you wear sweatshirts make sure to have a long sleeved t-shirt underneath and a vinyl windbreaker over it.
A stocking cap is the most important item for a runner to wear in the wintertime. This is because 90% of your body heat is lost through your head. It is not uncommon to see a runner wearing shorts and a t-shirt with a stocking cap and gloves. Because of your blood circulation while exercising these are the places that get cold first.
I don't check the weather every day before I go running but here is what I wear most days.