Yes, it takes some experimenting. You will make some mistakes in the learning process. With luck, they will be small mistakes.
When I set out to learn to dress for cold weather running, a more experienced runner told me if I wasn't cold when I started I was overdressed. I find that to be true for temperatures below freezing, more or less true in the 30s, less true in the 40s and 50s.
Once you go through a cycle of weather and learn what is appropriate at what temperature, you'll have fewer surprises; but there will still be surprises. You may guess wrong about how much to adapt for a given level of wind, or for a slower running speed. You may find that with a changed level of conditioning, you need a different level of clothing than you did for the same weather conditions.
Still, running in the cold can be quite enjoyable. It's really nice to not be drowning in my own sweat or worrying about hydration on a 30 minute run when the temperature drops below 55.
"Discipline is remembering what you want. " - David Campbell
Max Lifetime Weight, 221
SP Start Weight, 196.6
Initial SP Goal, 175
Current Goal on Ticker, 162
| current weight: -0.2 under