I agree it would be stupid to be unprepared. And I'm pretty outdoorsy myself though heat is a bigger concern then cold for me.
Even cave men were "prepared" with tools, weapons, adequate clothing and shelter. I don't think it would be fun to be dropped off nude on a glacier in a remote northern mountain range.
But living off the land, in the wilderness like the aformentioned Alaskan documentary would be pretty sweet. With a woman.
I know more dudes have to feel it.