Thanks so much for your reply carlotta. I'm back in Seattle, where unfortunately nothing ever fully dries. I'm thinking about getting a rain repellent running jacket that will double as my cycling jacket as I tend to be a minimalist; as well as running pants that can be used for cycling.

I really like your idea about the smart wool layer and tights; I might even be able to look somewhat cute in a skirt/tights once winter comes around.