The technical clothing available to us these days is amazing. The challenge is in how to use it throughout the fall and winter when conditions on any given ride can vary widely.
One of the biggest issues riding in cold weather is over dressing. When you overdress you sweat too much under the wind breaking fabrics - this gets everything wet. Once that happens it becomes hard to stay warm, particularly if the conditions change for the worse.
The best strategy for cold conditions is to layer your clothing. You can easily adjust how warm you are by taking on and off vests, caps, and wind jackets. It can be a bit of a pain, and your pockets can get full, but it will keep your body at the right temperature.