Normally I would agree with everything you said, Madscott!
Believe me, I have practically purchased an entire new wardrobe this autumn in preparation for my cold weather biking for the first time. I had nothing but inappropriate clothes before!- Baggy loose cotton sweaters, heavy coats, fashion gloves, berets, long dresses and skirts, cotton leggings, giant scarves, huge boots.... all totally USELESS for bike riding!
What was I thinking all these years??

DH was VERY understanding as I loaded up on merino base layers, helmet liners, gloves, socks, sweaters, hoodies, wind jackets, sweaters...you name it. Preparing for the cold. I know he is just so happy I love to bike with him now, and he loves seeing me getting into healthy shape. I showed him a drawer full of merino layers, and he said "Sweetie, I'm PROUD of you for being so determined to bike in the cold weather!". WHAT A MAN!!

I got two heavy switchback sweaters, two smartwool hoodies, a merino heavy vest, thermal windpro jacket, a gortex shell, several merino base layers to peel off and on, and I also picked up 3 all-wool turtlenecks at GoodWill on the cheap- one all cashmere, and one thick ribbed all merino turtleneck ($2.99!- my biggest steal)
And this just describes my torso layering system. We won't even get into my hands, legs and head layers...
The one thing I didn't have to buy was shoes. My Thinsulate hiking boots are working well and they fit in my pedal straps nicely and keep my feet very warm over heavy skiing knee socks.