Riding in the cold is one of those experiences that take you out of your comfort zone and you hate it while you’re doing it but it is very satisfying afterwards.
It’s actually not too bad with the kind of technologically advanced clothing that is available.
It starts with a will to want to do it.
Once that’s established you need to layer depending on how cold it is.
Start with Bontrager Base Layer long sleeve with a hood. It’s fabric is designed to wick away moisture and trap in heat at an ideal temperature. The hood is great, because if conditions are colf the back of the neck isn’t exposed and it the front part of the hood can zip up over your mouth. Also, it has thumb holes, those allow it to stay under the glove preventing skin from being exposed.
Then, typically I’ll add a standard summer jersey on top and/or/with a jacket. Your body will generate heat as you work, so the biggest key is keeping it in and fabric that will not become soaked with sweat, cycling apparel is designed for this.
Thermal tights are king here for cold cold conditions, more mild conditions can see the use of warmers and extreme conditions need both. Typically you’ll want to wear your standard shorts underneath the tights.
Things to stay away from are standard cotton clothes. They tend to become soaked with sweat and freezing you.
As far as riding itself, shorten your ride time, increase the intensity and don’t get wet and don’t stop.
And if the cold isn’t for you ride indoors on a trainer because it’s very convenient and a helluva workout.