First ride ever in the 20s. I was not layered correctly and ended up taking several breaks, mostly due to the headwind, but also to sort of balance my body temp (cool down the upper half, warm up the feet/hands).
I wear thermal tights under some stretchy jeans, a long sleeve baselayer, a hoodie, and a coat over that. Leather gloves w/ fleece lining. A beanie works fine on my head. I wore one pair of thick wool socks inside my running shoes and my toes got really cold at about mile 8 of 12 so I stopped and put on another pair, which was a mistake because my toes were cold evidently because my feet were sweating. After taking my shoes off and exposing my sweaty feet to the cold wind, it didn't matter how many socks I'd have installed, my toes were ice for the last 25 minutes.
I hope I have enough energy to make it home. Hopefully the wind will not shift and I'll have a sweet tailwind all the way.
Still a relatively new commuter at 9 weeks, learning new lessons every day.