Both sides have their advantages and their drawbacks. Wool is pretty good and rugged, so is waxed/oiled canvas, but they are also heavy. They are durable, but can reduce dexterity. Up until recently, no synthetics really compared too well. With the advent of these new synthetic laminated fleece items, I think we are seeing some really suitable alternatives to natural fibers. Rivers West is a product line of these type fleeces. They used to be the only ones making this stuff, but I see others have joined the wagon. These fabrics are quite durable, very warm, waterproof, windproof, and relatively lighter and less restricting. I grew up with canvas and wool, and they are my first love for outdoor clothing and I still use them when I can. The new fleece apparel is going to give them a fair run for their money. My primary hunting outfit is a suit made from this material, and it has proven itself quite well. Hunting coyotes above Estes Park Colorado in January I felt just fine sitting in the snow calling for hours. When my face got cold, I pulled up the balaclava and was as warm as I've ever been out in the field. The new fleece does seem to breath a little, but if you exert yourself without venting it properly, you are still going to end up sweating.
As for loft or fill, I think most of us here know that down is still considered a premium fill material, except when it gets wet. Some of the hollow fiber fills do come pretty close to duck feathers, and when they get wet they seem to fare considerably better in most cases. I've always been a fan of Qualofil, and if adding another half pound of fill keeps me just as warm, then I don't mind too much. The only time I got seriously cold in a sleeping bag was sleeping under a tent fly on a granite perch near the top of one of the fjords in central British Columbia coast during a heavy rain storm. Sometime in the middle of the night a stream formed cutting through my side of the fly, and so it was either sleep in the stream or out in the rain. That was a premium synthetic fill, and I am certain that a down bag would've been totally worthless then. I coulda used a good bivy bag that night.
Synthetics do have a problem with burning materials. I can sweep embers off my arm in a wool coat and not really notice anything unusual. Can't say the same for the fleece, though it doesn't automatically incinerate like some of the earlier synthetic materials used to either. In any case, if something does happen to my fleece gear, it has a lifetime warranty against such events.
I'm not a big fan of nylon/synthetic shells for clothing. They feel like I am wearing a plastic bag and make too much noise. Oilskins weren't much better. I suppose if you are going to wear a tent, then the nylon stuff is probably more convenient, but less durable.
I do miss my old Navy Pee Coat. That was a real comfort clothing item.
I have always been a fan of Pendleton wool blankets, even though they are way overpriced. I got me a blanket made from that new fleece stuff, and it is now my favorite tag along stowable. Another bonus is it don't itch me near as bad when I wrap up in it after a winter evening in the hot tub.