Recently I have been working on a number of design projects and seen a few others starting to produce results. Even after a lot of effort the results may be of limited value. Eventually a well thought out "system" will allow one to use less clothing, carry less weight with better protection from the elements, all while being more versatile. Think a seamless approach, head to foot.
I think to design well, you need a beginner's mind, an open mind. The student's mind. And enough experience to know what really does work and why.
Below are a couple of good thoughts for you. I don't agree with everything listed in the blog post. I think tucking your pants into a modern gaitered boot (Phantom and Batura) for example is a bad idea. Tucking your pants is simply a faster way to get cold, wet feet eventually.
But when thinking of a "clothing system" these two are good info worth remembering.