Fall is turning chilly with the temps in the low 40s this morning and going colder tomorrow. I found this article by Elizabeth on Bike Commuters, written for Chicago to be useful. Certainly Portland is not as cold as Chicago, but the east Gorge Wind provides subzero chill factors during Winter and so I always know I can learn from others.
From her post:
I tend to over-think things a lot! This quality of mine can be both good and bad. What I like about fall/winter riding is that dressing for it really is easy – you just need to know the purpose of each layer and best fabric for that task. Aside from those days when I start pondering other gear, layering is really quite easy – and leaves me feeling always prepared.