Boots and gloves are probably the 2 most subjective pieces of clothing one needs to sort out. I have a couple friends that need WAY more boot/glove insulation than I do to stay comfortable. Tough guys who spend countless days out in COLD weather. They just need more.
The other balance one needs to find is support vs. dead air space. A snug fitting boot that locks your feet into place feels great on rough terrain, but, dead-air space insulates well. There's a balance there somewhere, it's different for everyone.
