We've had many great rundowns of this topic in the winter cycling forum here.

In late autumn when it's raining and dark, I was wearing a regular wind-breaker with sweaters of varying thickness underneath. Using layers, ideally of wool or wicking fabric, will make it comfortable. The wind breaker I wore is a MEC one that has armpit zippers so that is nice if it's sunny but still cool. I have also acquired a campmor rain cape and it's nice and roomy underneath so I will be using that until the rain turns to snow, since I can wear whatever kinds of sweaters I need to underneath it. I highly recommend the cape cold rains.

When it becomes full-on winter I have a high-vis construction parka that I wear. My choice of winter footwear is water proof sorel boots. I ride on BMX pedals exclusively in the winter and they grip the boots well and my feet have yet to get wet or cold, despite riding in temps below -20C. The big sorel boots show up in thrift shops around here too. If the weather is mild and dry I will usually just wear wool slacks from the thrift store. When it gets cold I put on long johns... and if it's snowy or the roads are sloppy, I wear splash pants on top of that. It was a great setup for a 10km stop and go commute through town. I might gear down a bit if I were doing longer or faster rides.

The other key part of getup was a scarf... could wrap it more like a balaclava if it was windy but most of the time I use it just around the neck as I rarely wore anything on my head... let all the heat out that way and if I was getting too hot it's easy to unzip the coat a bit and let some air out without letting draft in, the scarf is essential gear for me.

If you live someplace where winter doesn't get too cold, you could likely get by using galoshes over your shoes to keep your feet dry and warm. They're also nice in the fall/spring when the big boots are too warm.