Winter commuters learn to dress for the temperature. They will start out slightly underdressed , and therefore feeling a little cold. In a couple miles they are warmed up and cranking along. Once underway, most winter commuters will regulate temperature by work level rather than stop and change. Rain gear is the exception.
Recreational riders tend to be out longer, and have stops planned, to eat, chat or whatever.
In these cases, where major changes of activity are planned, the layering principal comes on strong. Unlike commuters, trail riders can not plan on ducking into a store to warm up and must be prepared for breakdowns and changes in the weather. I'm not about to suggest you enroll in a meteorology class, but there is a great deal to be said for just paying attention to what works for you. If one ride is too cold, learn to think of what you wore as something that need the assistance of another layer. This almost implies that you will make a few mistakes along the way, and over dress or under dress a few times till you get it all figured out.