Currently my dress is simple ...
Feet: DeFeet Woolie socks under Brooks Pure Connect Shoes
Legs: Nike lightweight running tights under a lightweight pair of running pants
Chest: Under Armor thermal long sleeve shirt under a Bontrager cycling windproof jacket with underarm zippered vents
Hands: Lightweight running gloves
Head: Gore cycling balaclava
While running this keeps me toasty in 20F+ weather. Any colder and I will have to rethink what is on my legs.