I like the new windblocker fleece a lot, as it saves having to wear a shell over the top on windy days. I recently bought a 200 weight windblocker jacket at REI and have basically retired my older model. Lotsa layers is the key. A bottom layer of synthetic polypropylene underware is a good start-using either the middleweight or expedition weight-or carry both like I do (Big pack!). REI's MTS or Patagonia's Capeline lines are good examples of the genre. BTW, the synthetic undies are great for hiking all year, they don't hold sweat like cotton. A button down nylon shirt-or, on a very cold day one of the micro fleece shirts (similar to the old cotton "chamois" except synthetic and hydrophobic) topped by a windblocker fleece jacket of 200 or 300 weight (bigger number, heavier weight) will get you pretty close.
A gore-tex or other proprietary waterproof/breathable shell and pants covers it all. Cotton is to be avoided at all costs. The "Fabric of Death" is nature's own evaporative cooler. The same features that make it so comfortable on a hot summer day turn it into a short cut to hypothermia on a cold wet windy day. Adding or removing layers of the above,depending on your level of exertion is most of the battle. A nice extra is a down vest, which stuffs up into a small, light carry, keeping the torso warm. The best ones feature a "microfiber" material which helps shed water and block wind. Mountain Hardwear makes a really nice one.
We often forget how much heat is lost though the head and hands. A nice fleece or wool/poly blend stocking cap is a great help (also if one tends to sleep cold in a three season bag) as are a pair of gloves. I like the fleece ones with the little rubber pads, so when I fall down on the trail trying to keep up with Mike, I have some traction on the way up. Finally, a wet pair of boots doesn't help. Whatever waterproofing is suggested for a boot type helps keep the sox dry. I like a thin polypro liner next to the skin and a wool or wool blend outer sock from someone like Wigwam, Thorlo or Smartwool.
The above are not in the Army surplus price range. Remember- the Army takes low bidder.... Both Sierra Trading Post and REI-Outlet offer discontinueds, irregulars and last years models for much less than retail.
When all else fails, nothing beats a dog for putting out BTUs in a small enclosed space. -Randy
"The trail is the thing, not the end of the trail. Travel too fast and you miss all you are traveling for." -Louis L'Amour