I have a pair of windproof in the front tights from Performance that I LOVE. They are super warm, and good in light rain, even. My PI Calientoes are good down into the 50's, but lower than that I'd want more serious foot warmth. Unfortunately, I haven't figured out what that is, yet. A Bolero would be good for days when it is cool in the morning then warm in the afternoon. I also have a jacket from Early Winters that is fleece, but windproof in the front/breatheable in the back- that's nice to layer. I have a couple wind vests- but I don't know how much good they do. I wouldn't buy one of those unless you have money to spare. But I have a nice Shebeast wind jacket that is super light that layers nicely.
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"...I'm like the cycling version of the guy in Flowers for Algernon." Mike Magnuson