I wear headbands always (to keep sweat out of my eyes), but in the winter switch to the ones that are shaped to cover ears and a little thicker. I like water resistant gloves that are not too bulky. I'm already using arm warmers and will soon be wearing leg warmers. When it gets colder yet I will wear a long sleeve jersey over arm warmers and finally two long sleeve jerseys over arm warmers. Oh and booties just for warmth. That's barely adequate for 20 mile commute in mid to upper 30s- typical "colder" commute in PNW. No tights, and no jacket but sometimes wish I had one. Or maybe a rain cape.