I observed how Mors Kochansky was dressed during his DVD "Clothing, Sleeping Bag and Sleep" and his layering system is well thought out. He gave his lecture somewhere in Alberta during the winter at 0°F but for somebody active and working with fire, so his system is versatile. Of course it depends on the weather and the condition.

Basically you need top and bottom polypro or similar (Capilene, etc.) underwear to wick moisture away quickly that sticks to your skin with a minimum of air space without being restrictive. Then on the top you add as many commando wool sweater (with patches) like Brigade Quartermaster's Woolly Pully (they began their business by selling this item during the 70s I think, so you can't go wrong with them) I don't know if your sweatshirts and t-shirts are cotton btw but unless it's during summer, we've all heard "cotton kill".



Same for the pants, wool pants with suspenders (the elbow patches on the commando sweater are well positioned for protecting the wool against the abrasion from the suspenders)

Then a very versatile piece of clothing that adds insulation is a down or synthetic vest, some have a kidney warmer back and have a crew neck baseball knit type of collar to allow room for wearing heavy scarves and putting it under a more serious jacket and are reversible, with blaze orange on one side like this:



Then it's the environment layer, a windbreaker with hood and nylon windpants.

Of course you also need protection for the hands, moskito nets, wide brim cowboy hats are useful to protect against the rain and make a serious difference in fanning to get a fire going, orange bandanas, decent broken in boots with many spare of wool socks, etc. And the wool or synthetic blaze orange watchcap is really versatile and as useful in cold weather as in desert environment and is very compact so you should always have a warm watch cap in your pack even during summer excursions. Since a large percentage of body heat is lost from the neck and head, it's crucial to cover these area.