Merino underwear and socks next to skin. If it's really cold then two merino tops and bottoms. No cotton - not even your boxers. Merino will keep sweat/moisture off the surface of the skin, wick and stop you feeling sweaty/clammy. Much better than polyester or polyprop underwear. Two pairs of socks also works when bloody cold but one must be very thin.
Fleece mid layer top and if really cold trousers too. This is your main insulation layer. No membranes as they will restrict moisture exiting the system.
Outer layer should be Gore Tex or another high quality membrane. Not sweat in the bin bag cheep stuff. This will allow the sweat to exit the system. Water sucks away body heat 30 times faster than air so having a good quality breathable on when walking up hills is important - keeping the sweat in gets you cold very quickly. Sweat/Water really is the big enemy and needs to be eradicated.
When dressed up like this, well insulated and dry, you will be loosing about 40% of remaining body heat through hands and head. This can be used to your advantage when working hard. Gloves and hat off when walking up hills and sweating will regulate heat well. Put a pair of gloves and a good beanie (or even better a fleece lined waterproof cap) on when you get to the top and have stopped sweating or when you start feeling cold.
I find that in cold but no wind I'm fine with a baseball cap and fingerless fleece gloves. As soon as the wind starts blowing over 10 knots the the wind chill forces me to put on the big hat and waterproof gloves. My back pack usually has an assortment of hats and gloves in it - putting on a dry pair of gloves when your current ones are wet through warms the hands very quickly. Same with a hat. And they don't take up much space.
If in a high seat then all bets are off. Really tough to stay warm without something like a duck down mid layer and a 5mm neoprene seat pad. This is really where the heated jacket/boots come into their own, or the Hotties. Again, head hands and feet need wrapping up warm.
I always find that lingering over the gralloch with you hands inside the beast for a while is fabulous for getting heat back into your fingers.
I've done this for a living for 35 years with a certain amount of success, having had the benefit of testing a lot of fabrics on a lot of people in extreme conditions. There is no such thing as totally warm, dry and comfortable when the conditions are really cold/wet, but the above is about as good as it gets if you're going to go out in it.
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