Bookshelf

Techie

• Unauthorised Access: Physical Penetration Testing For IT Security Teams by Wil Allsopp.
• Social Engineering: The Art of Human Hacking by Christopher Hadnagy
• Practical Lock Picking: A Physical Penetration Tester's Training Guide by Deviant Ollam
• The Art of Deception: Controlling the Human Element of Security by Kevin Mitnick
• Hacking: The Art of Exploitation by Jon Erickson and Hacking Exposed by Stuart McClure and others.
• Nmap Network Scanning: The Official Nmap Project Guide to Network Discovery and Security Scanning by Fyodor
• The Shellcoder's Handbook: Discovering and Exploiting Security Holes by several authors
• Snort IDS and IPS Toolkit (Jay Beale's Open Source Security) by several authors
• Schneier on Security by Bruce Schneier
• The Red Team Handbook (PDF)
• The Practice Of Network Security Monitoring, Richard Bejtlich
• Metasploit, The Penetration Tester's Guide, David Kennedy
• Violent Python: A Cookbook for Hackers, Forensic Analysts, Penetration Testers and Security Engineers, TJ O'Connor
• Rtfm: Red Team Field Manual, Ben Clark
• Open Source Intelligence Techniques - 3rd edition (2014) by Michael Bazzell.
• Joint Doctrine Note 1-16, “Command Red Team.” by the U.S. Department of Defense.

Non-Techie

• The Mission, The Men, and Me: Lessons from a Former Delta Force Commander, Pete Blaber
• The Art of War, Sun Tzu
• The Book of Five Rings, Miyamoto Musashi
• Inside Delta Force, Eric Haney
• Human Intelligence, Counterterrorism, and National Leadership: A Practical Guide, Gary Berntsen
• Maneuver Warfare Handbook (Westview Special Studies in Military Affairs), William S Lind
• Silent Warfare: Understanding the World of Intelligence, Abram N. Shulsky
• The Gift of Fear and Other Survival Signals that Protect Us From Violence, Gavin de Becker
• Red Teams and Counterterrorism Training, Stephen Sloan
• Escape the Wolf – Personal Security Handbook for the Traveling Professional, Clint Emerson
• On Killing: The Psychological Cost of Learning to Kill in War and Society, Dave Grossman
• Killer Elite: The Inside Story of America's Most Secret Special Operations Team, Michael Smith
• Chosen Soldier, Dick Couch
• KODO: Ancient Ways: Lessons in the Spiritual Life of the Warrior/Martial Artist , Kensho Furuya
• Man in the Shadows: Inside the Middle East Crisis with a Director of Israel's Mossad, Efraim Halevy
• The Essence of Aikido: Spiritual Teachings of Morihei Ueshiba, Morihei Ueshiba
• Let My People Go Surfing: The Education of a Reluctant Businessman, Yvon Chouinard
• Emergency: This Book Will Save Your Life, Neil Strauss
• The Rock Warrior's Way: Mental Training for Climbers, Arno Ilgner
• Brotherhood of Warriors: Behind Enemy Lines with a Commando in One of the World's Most Elite Counterterrorism Units, Aaron Cohen
• Powerful Peace: A Navy SEAL’s Lessons on Peace from a Lifetime at War, Rob DuBois
• The Red Circle, Brandon Webb
• The Art of Intelligence: Lessons from a Life in the CIA's Clandestine Service, Henry A. Crumpton
• The Unfettered Mind: Writings from a Zen Master to a Master Swordsman. By Takuan Soho.
• Left of Bang: How the Marine Corps' Combat Hunter Program Can Save Your Life, by Patrick Van Horne.
• Team of Teams, by Gen. Stanley McChrystal.
• Red Team: How to Succeed By Thinking Like the Enemy, by Micah Zenko.
• Extreme Ownership: How U.S. Navy SEALs Lead and Win, by Jocko Willink and Leif Babin.
• About Face: The Odyssey of an American Warrior, Colonel David H. Hackworth.

For Fun

• The Activity, Nathan Edmondson and Mitch Gerads
• Brad Thor's Scot Harvath collection
• The Volunteer: The Incredible True Story of an Israeli Spy on the Trail of International Terrorists, Michael Ross
• Dirty Wars: The World Is A Battlefield, Jeremy Scahill
• Navy SEAL Sniper: An Intimate Look at the Sniper of the 21st Century, Glen Doherty and Brandon Webb
• Spies Against Armageddon: Inside Israel's Secret Wars, Dan Raviv and Yossi Melman

Also, check the Red Team Journal's Bookshelf for more great books.