I wasn’t comfortable with my skill level for my daily commute (45 miles one way) until the temperature had dropped. The first morning was brutal. My jacket was fine, and the insulated jeans I used for ice fishing were also excellent for riding. But I discovered my heavy winter gloves had blown a seam, and my face was frozen even inside my full face helmet. A very brutal ride.
I picked up a balaclava that day, before I rode home, and it made me worlds warmer. I also grabbed a pair of snowmobile gloves from Tractor Supply. They aren’t ideal, in that $13 gloves don’t really have the flexibility you might like, but they’re warm, and the gauntlet cuffs come up over the sleeves on my coat, keeping the cold air out.