A messenger bag is a great entrée into the world of men’s bags. As a daily option for carrying around documents, magazines, books, a laptop, your assortment of chargers, office supplies, and so on, it hits all the right notes. Less formal than a briefcase and—if you choose the right material—more grown up than a backpack, a messenger bag is perfect for the man about town and the guy on the go.
While you can get a messenger bag (also sometimes called a courier bag) in other materials like canvas, for example, I recommend investing in one made of leather. Leather will last longer and age well. A worn in leather bag has infinite amounts of character. Mine is 15+ years old.
A leather messenger bag is also much more versatile. It’s usually the first one I’ll grab if I’m running out of the house dressed casually, but also looks great when you want to look sharp but relaxed.