Defy Recon Messenger Bag ($322 @ Amazon.com)
A big part of what makes vintage items cool is the story that comes along with them — and these vintage bags from Defy have a badass story to tell, which makes them some of the best messenger bags for men.
Each Recon is made from battle-deployed M35 military canvas and/or vinyl truck tarps, along with vintage Austri Alpin Cobra buckles used by the U.S. Special Forces. (That’s why the bags come already looking worn-in.) The strap is an old seat belt and the trim is made from bike inner tubes. But while the outside and material are both rugged, the innards are roomy and built to support a 17-inch laptop, books, journals, and maps of enemy territory.