This Winter I'm doing it completely different from previous ones - in the past I'd layer skin out with my cycling clothes, complete change at work and probably shower. Probably four layers at what we call extreme cold here. It's been mostly mild this year, barely below freezing in the mornings, and I'm wearing street/office clothes. Shirt/windbreaker, third layer is a cycling rain jacket or I've used a jersey once or twice as a sweater over my my shirt.
So, 2 or 3 layers.