It takes time to learn what clothing goes with what temperature. If you’re coming to running from cycling, your temperature to clothing translation algorithm will be off. If you’re new to running, it will also be off, though not as badly.
Imagine it is a nice, 65F day. If I want to go for a walk, I will wear a long-sleeved shirt or light jacket, shorts, and shoes. If I want to go cycling, I’ll wear earmuffs, gloves, bib shorts, a short-sleeved cycling shirt, and arm warmers.
If I want to go running, I’ll wear running shorts and a light shirt. Even then, I will be too warm.
Imagine it is 45F. When walking, I’ll wear a light jacket, pants, and shoes. I might wear earmuffs if I’m walking far, as I hate having cold ears. When cycling, I’ll wear earmuffs, gloves, bib tights, a short-sleeved cycling shirt, a cycling jacket, and possibly a base layer shirt.
When running, I’ll wear running shorts and a light shirt. Even then, I may be too warm.
Imagine it is 35F… You get the idea. For running, I’ll still be in the shorts and a light shirt. Though I won’t be too warm this time. It needs to be below freezing, or near freezing and windy, for me to wear a long-sleeved shirt, gloves, or earmuffs.
I’ve learned this via experimentation. Thankfully my runs are short enough the only penalty for bad clothing choices has been getting overly sweaty. If I were doing longer runs, overdressing could lead to dehydration.
Wind, unfortunately, complicates picking clothing when it’s cold out. If I’m running into the wind, I’ll be too cold on the way out, too warm on the way back. Tailwinds mean too much retained heat. If part of my run is shielded from the wind and part not, I’ll alternate between too hot and too cold.
What clothing works best for you can only be determined by experimentation and answering one question: would you rather be too cold for the first mile or two, then feel pleasant, or warm for the first mile, then feel too hot?
While you’re learning, keep an eye out on extremities. You may find parts of you are cold when the rest of you is not. Use shorter runs to check for temperature sensitivity. Best not to find out you need wool socks 7 miles from home!