Start with high-confidence outdoor skills books, then narrow by subgenre or adjacent topics.
Basic Illustrated Wilderness First Aid
William W. Forgey M.D., William W. Forgey
The Winter Survival Handbook
Tim MacWelch, The Editors of Outdoor Life
Essential Wilderness Navigation
Craig Caudill, Tracy Trimble
Mountaineering: the Freedom of the Hills
Mountaineers Books, The Mountaineers Club
Primitive Technology
John Plant