Eeeee! We argue, er, discuss this frequently... I use what I know works and it's pretty unfashionable - assuming a downstate NY winter as one of your worst cases, I'd go with loose and layers. I mean, REALLY loose - US Army properly fitted arctic clothing type loose (which happens to work just as well in hot weather - tight clothes are miserable). Outer layer should be pretty windproof and fairly water repellant. It also should be tough as all get out. My #1 choice for this (excluding raingear) is NyCo sateen windproof cloth (either 50-50 or 40-60) with Quarpel treatment, but there are other choices. Tight weave wool-nylon stuff is good and it is quieter in the thick stuff than sateen if you're interested in other natural alternatives. There are good synthetics, but I don't suggest them as outer wear around fires - just my opinion.<br><br>As a very good general rule, eliminate all 100% cotton stuff. However... I feel - and it is my experience - that cotton underwear is OK most of the time. It does mean that you should keep a spare undershirt and drawers in your kit, though. Undergarments serve an often overlooked purpose in extended wear situations - they reduce the soiling and contamination of inner layers from body oils and grime. Silk is better than cotton, especially if you're thinking of EDC wear. Most of the synthetics can get pretty stinky... although there is no question in my mind about the performance advantage.<br><br>Rain gear is miserable stuff no matter what. I'm pretty sure there are no miracles out there... I have a gore-tex 3/4 parka I like, but it is not the trick for extended / heavy rain. I have some real rain gear for that - of course, it's a swamp inside. Rain gear is just too big a topic all by itself... sometimes I just allow the wet and dry off when I get a chance - but not in cool weather.<br><br>I think everyone else covered other things I would say. I agree with P_L about the separate wind layer and pile jacket, having used my wife as a tester on all manner of both. I use a pile liner more and more often now - but it's just one of my available layers and I'm careful about if and when I use it as an outer layer.<br><br>Regards,<br><br>Tom