Hi Tigerjaw,
Military Cotton/Poly Clothing will suit a reasonable range of temperatures and environmental conditions but when conditions start to become a little more demanding or extreme then specialist clothing is required.
Most Military Cotton/Poly mixes aren't generally windproof so in cold windy conditions they are pretty useless. By cold I mean anything less than around 10C 50F. In cold and wet conditions i.e. -5 to 10C, 23F to 50F they are very poor choices without a waterproof overtrouser.
There are available windproof military clothing made from cotton garbadine material, being more expensive than general poly/cotton, such as found here at;
http://www.sasskit.co.uk/products/militaryclothing/sassmock.htmThen there is ventile, which is higher specified than the cotton garbadine. Ventile is either single or double layer. Double layer is generally regarded as being waterproof and windproof. Single layer just windproof. Double layer Ventile is twice the weight of single layer ventile.
http://www.west-winds.co.uk/ventilejackets.htmAgain Ventile is very breathable and some folks will live with its disadvantages when compared to Goretex. Goretex is completely waterproof but it is not as breathable compared to Ventile. So you may end up getting just as damp as single layer Ventile. Ventile is excellent for temperatures below -5C 23F being reasonably dry conditions. Ventile is also very long lasting, tough, easy and quiet to wear and field repairs can be made easily.
I also find that Gore Windstopper or Polartec Windbloc fleece is also very good for high activity cold dry i.e. -5C to 10C conditions.
http://www.jackson-sports.com/Models.aspx?ModelID=154Goretex jackets are excellent as well, there really is nothing else out there that will protect from the wind and rain for the money. There are also so many different types of Goretex out there with each one specified for slighlty different conditions. I recently got another jacket made from Goretex Saturn, which was on sale. It is comfortable, has easy to handle fabric and is reasonably lightweight.
http://www.wildtrak.com/product.asp?id=1138Military Goretex usually refered to as ECWS or MVP can be purchased more cheaply if you like camo. This Goretex is pretty good being tough and reliable being manufactured for military conditions but generally doesn't have the refinement of the more expensive civilian Goretex products.
I prefer Merino wool or merino wool/silk for base layer undergarments and a wool pullover instead of conventional fleece midlayer despite the heavier weight.
These tweedy trousers look interesting for that country gent look.
http://www.fifecountry.co.uk/PRODUCT_DETAILS.php?pid=632&cid=29