Thinking from the bottom up

I just bought a pair of Red Wing boots to replace my old winter boots. They were an extremely strange pair of boots, shaped like a pair of Clark's chukkas, but fur lined and made of some sort of hard, dark leather. Unfortunately, they were also from the 60's or 70's, and cracked along the sides.

So I've been thinking about shoes. Plotting and planning about making them. I have some ideas, I have some thick wools and leathers, and I'm eying some waxed linen thread at my school's resale shop.

A while back I tried to make a little wool shoe:

Which is a good jumping off point. And I've been drawing shoes too:

Hopefully I can get to a scanner soon, sorry for the awful photo-of-a-drawing. I was working from images of old armor--Leg armor called graves and cuisses. And samurai armor as well, most of it is made from bamboo and fabric, and I feel like I can emulate that in boiled leather and wool.

I also want to try doing some cut work for more delicate, lace like boots.

Some shoes I'm looking at: