+1 Ex Officio boxer briefs. Maybe the best underwear for men ever made.

These have no real properties for cold weather but IME hot or cold, they don't loose shape after hours of vigorous hiking or running and that means no chaffing which means they hold up.

I have a UA cold weather long sleeve mock turtle neck and its just okay. Could get the same results from a cheaper brand.

Gloves? Not much help there. Having gloves on you I think is more important than if they are waterproof and such. My water proof gloves are cycling ' lobster lobster' glove made by Pearl Izumi.

I wore D-3A army issue gloves, (black leather) for years with the issued wool liners and they did fairly well. Still have all my fingers!