The Definitive Guide To Messenger Bags

They need little to no introduction. They can be found just about everywhere in an urban setting nowadays. As far as style options are concerned, they’re one of the original hipster staples. Messenger bags for men are a safe bet when it comes to selecting an accessory that’s both practical and cool. They come in various sizes but are typically large enough to accommodate a guy’s most frequently used possessions—from his can of spray paint to his course books, to his latest generation MacBook Air and Beats by Dre headphones.

Men’s messenger bags came (back) into style about a decade ago, when they virtually invaded cities all around the globe, from London and Milan to NYC and Seattle, to Tokyo and Sydney. But where do they come from historically? What sizes and materials do they come in? And, as most guys would be prone to ask—how are they best worn? Today’s article tries to answer all those questions, so just read on to find out. 

What is a messenger bag? 

The definition of a messenger bag isn’t that hard to infer, is it? It’s a style of bag, originally designed for carrying postal messages. It comes with a long strap, to be worn across the body or the shoulder, and it can be designed in a wide range of materials. More often than not, the sack of messenger bags is made of canvas, but leather and plastic variants are also rather common. 

A brief history of the messenger bag

Messenger bags also go by a handful of other names, including carryalls, and courier bags. As you’ve probably guessed by now, they were initially used for carrying letters and other postal dispatches, even as early on as ancient times. Among others, bike couriers and Pony Express staff were the first to carry messenger bags. And nowadays in the UK, some couriers of the Royal Mail use oversized messenger bags instead of regular Postbags.

The first modern messenger bag was actually the bag worn by utility linemen in the 1950s. It was designed by the De Martini Global Canvas Company and its purpose was to accommodate all the tools that linemen needed when going up utility poles to fix them. The initial messenger bag was made of cotton canvas and lined with waterproof fabric. The shoulder strap was also made of cotton and webbed, the bag closed with two straps and it also had a pocket on the inside for invoices. These bags were not sold in stores but issued to and by various messenger companies based in New York.

Globe Canvas was the main bag supplier for most such companies in New York during the 70s and 80s. Back then, messengers received the bags from their employers and you could tell who worked for whom only by the color of their bag. The De Martini bag got a facelift in 1984 when John Peters first made it nylon and added binding, as well as buckles and light-reflective stripes. And so, with these simple additions, the fashion craze for messenger bags begun. It’s worth noting that before these bags specifically made for bike riders emerged, fashion brands manufactured similar products modeled after map case bags used by the military. They have been in use for over one hundred years now.

Cool Messenger Bags for Men: Pros & Cons

Men who walk or bike a lot, who typically carry laptops, and who, overall, are out and about on the regular, will have repeatedly asked themselves (and their buddies, better halves, bros, moms, etc.) this question as old as time: “Are messenger bags better than backpacks?”

To start you off, we’ll play it safe and say that it all depends. Also, unless you live and work in an urban setting, where most men carry some sort of bag for their personal effects, expect to be stared at and even screened by security. And now, let’s delve right into it—what are the pros and what are the cons of messenger bags?


  1. They are more professional than other options, in both form and function

Like most guys with a white collar job nowadays, you probably need to carry your laptop from point A to point B, every now and then. Maybe you work from home on most days, but have the occasional business meeting downtown. Maybe you freelance and need to bring your laptop to a networking or brainstorming session. Maybe you just commute to work. Whichever the case may be, the messenger bag is the smarter option, in terms of both style and functionality. To put it simply, it’s bigger than a fanny pack (cute, but not suited for larger items), and just about as big as most backpacks. Yet, unlike a backpack, a messenger bag will look pretty similar to a professional laptop bag. Bonus: it will also help you to avoid looking like a dorky collegiate kid.

  1. It’s far easier to find your stuff

You need a pen to quickly write something down. Your phone is ringing off the hook, in some nook or cranny of your backpack. Meanwhile, you’re fumbling for your items like crazy, arms behind your back as if you were giving yourself a weird kind of reversed hug. Forget that kind of discomfort and wear a messenger bag instead. With all their inner compartments and pockets, it becomes a breeze to have quick access to an item you need right now (and not five minutes later, when you’ve finally managed to unload the backpack off your back).


  1. Not all that comfortable for bikers

Biking around town in the warm season can be fun—or it can be a terrible hassle. It depends on the town, of course, on the purpose of your journey (leisure or business?), but it also has to do with how you come equipped. Any guy who rides a bike on the regular, and occasionally needs to carry around bulkier stuff, like a laptop, a book or two, and/or assignments for school will tell you that backpacks are a last resort. They will make your back sweat like crazy and are generally only suitable for longer trips, which require you to carry a load. Messenger bags can be more comfy for shorter trips when you need to make several stops and aren’t carrying much. However, they will still be uncomfortable for the following reasons:

  • Since they hang low on your back, they will still make you sweat a bit; 
  • They can throw off your balance on the bike if overloaded;
  • They can seriously stress your shoulder on trips that are longer than a couple of miles. 

For all the reasons above, seasoned urban bikers recommend panniers, rucksacks, or luggage carriers in most scenarios. The only exception is when, say, you’re only headed downtown to work on your laptop for a few hours and then meet friends for drinks.

  1. Less stable than a backpack

Building on the above point, even if you don’t bike, you’re going to find that messenger bags are slightly more unwieldy than backpacks at times. If you’re commuting in rainy weather, for instance, and your bag doesn’t come with a shoulder strap that has a good grip, the bag is going to keep sliding off. Similarly, if you need to carry a heavier load, your shoulder will quickly go sore with a messenger bag—which would not be the case with a backpack. All in all, the age-old ‘backpack vs messenger bag for men’ debate boils down to two essentials: 

  • How much you need to carry (and for how long). If it’s anything heavier than a laptop (and maybe a book or two), opt for a backpack, since it has better weight distribution.
  • How well-designed your messenger bag is. A good bag will come with stabilizing padding on the shoulder strap. 

So, should men really wear messenger bags?

No, men should definitely not wear messenger bags. Unless, of course…

  • They want to look urbane and classy. If you want to look dowdy, boring, or with the sense of style of a kid in junior high, then go for a backpack.
  • They want to be able to choose from a wide range of designs, fabrics, and sizes. Go with a regular 70-gallon backpack. Or a tiny fanny pack. They’re clearly better. And they will also make you look very professional.
  • They want to be able to reach their items quickly. Who needs all those inner pockets anyway? Why not just wear a canvas sack instead?
  • They want comfort. Sure, you could opt for a one-strap sling-back rucksack. Who wouldn’t want a load single strap cutting into their back?

Oh, who are you kidding? Of course, you do. And you can, if you start sporting messenger bags. Yes, it’s entirely acceptable for men to wear them, especially if they commute and need to carry around books, notebooks, or laptops. Unlike rucksacks or backpacks, they can still preserve a professional look. And, on the upside, they’re also appropriate for men past their twenties. Your dad is probably not going to wear one anytime soon (unless your dad is someone hip and trendy, of course), but messenger bags are perfectly suitable for professional males ages 30 to 50—and, with a bit of a sense of style, even upwards of that age.

At Mustache Trading, we sell both leather backpacks and messenger bags that are high quality and affordable. Shop today!