For some reason I keep reading the name of this thread as "All my Lawyers are soaked ..."
I have a layering system that works for me but it can change somewhat depending on the worse conditions I anticipate encountering, strenuousness of the trek, and distance and time in the field.
1. A wicking long john layer or a heavier long john contributing to warmth. I don't use wool of any sort for this layer as it can be irritating if ambient temps go up and the finer wools that are always comfortable don't hold up very well.
2. A warm layer, usually a wool shirt. I must have over a half dozen Pendletons ... a couple hand me downs from prior generations!
3. An optional layer of a fleece vest or sweatshirt or a warm wool sweater.
4. For stops, precipitation, exposure or any other need for protection I pack a goretex or similar jacket (and sometimes pants). Depending on conditions, I may add a heavier fleece liner in the jacket. Combining layers 3 and 4 is rare as it builds up too much heat and perspiration while hiking, especially uphill.
I carry up to three different gloves, lightweight liner, fleece and mittens plus a spare or two. These are layered up similar to the body layers.
For hats I carry a fleece headband and a heavy wool Coast Guard watch cap. Combined with the hood on the jacket this has been adequate.
I also carry a fleece neck warmer and a balackava rarely used but greatly appreciated when needed.
This has worked well for many years ... but I've had no aspiration to do the Bonds in winter.