>>2845972Not the guy, but for outdoor shoes you could do worse than a pair of Alfa M77. Opinions are divided on them, but for leather shell boots they're very cheap, and will last long with very basic care. Also buy insoles (Sof Sole Airr Orthotic are great for ergonomics, and the wool insoles from Sara Duodji if you get wet), wool socks (Alaska Sokken, 2+ pairs), and the Alfa Full Grain Leather Care Kit. Price might be a bit steep for it all, but still less than a modern pair of Gore-Tex boots, which work great until they suddenly don't.
For jackets, you're right. Your base layer is your wool underwear, it creates a layer of air that is heated by your body heat. The shell jacket keeps wind from blowing into this layer of air and cooling you down, and cold rain from seeping into it and cooling you down. If that is not enough, you wear a fleece or wool sweater over your underwear to further insulate. If that is not enough it's because it's freezing cold, and you might want to wear a down jacket over the sweater, under the shell jacket. For most, a nice thick wool sweater will suffice. Your jacket should therefore be sized generously enough to wear enough clothes under without squeezing them tight.
You might find it too hot or clammy to wear a sweater while you're moving, since your body generates more heat under exertion. Likewise, your body doesn't produce as much heat when you're resting, so you might want to wear your sweater to stay warm then.
There's not much to add to this or what
>>2845946 has written and linked to, now you need to go out and see what works for you.
You can find alright gear for cheap in Sport Outlet and Stormberg stores. Designs and solutions might be a bit dated compared to Norrøna/Arcteryx, but it works well enough. If you're going to spend bigly, spend your money on quality wool garments. You can rent some equipment at BUA if you have one near you.
