Updated on Jan 27, 2017. 

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?

THE UPSIDE

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.

 

2. 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).

 

THE DOWNSIDES

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.

2. 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.

 

Military canvas messenger bag for men, with leather-padded 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?

You don’t want to look cool, comfortable, and hip like this guy, do you?

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 any time 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.

Men’s messenger bags – A quick style guide

So, wait, we actually mean to tell you that it’s okay for men to wear bags?! But aren’t man purses totally ridiculous? If you live in the 90s, or model your life after the philosophy of popular movie franchise The Hangover, then, yes, bags for men are a total no-no. For the rest of you guys, welcome to a more comfortable and style-conscious life. Today, we’ll help you explore all the different types, designs, fabrics, and sizes of messenger bags. You’ll walk away at the end of this article feeling just as comfortable with your masculinity and just possibly a wee bit more stylin’.

The 7 main types of messenger bags for men

#1 The Satchel

Satchels resemble briefcases, in the sense that they’re defined by the presence of two vertical straps for the buckles which help close the bag. Other than that, they can vary in terms of size, style, and design.

 

#2 The Vertical Messenger Bag

Most messenger bags have a longer width than height. With vertical bags, you’ve guessed it, just the opposite is true. Like regular messenger bags, they come in a wide range of fabrics, including (but not limited to) canvas and leather.

#3 The Briefcase

The main characteristic of such a bag is the fact that it’s made of leather. And then, what sets it apart from other types of leather bags for men is its retro schoolboy-inspired design. A leather briefcase will always feature a frontal flap, with one or two buckle straps for fastening the bag shut, plus (optionally) a corresponding number of outer front pockets.

Full grain heavy-duty leather briefcase

#4 The Military Bag

Rough, rugged, and versatile, military bags are inspired by actual army items. They are almost always made of canvas, but can also include leather elements, as well as badges, or text in military-inspired fonts. They have several pockets, both on the inside, as well as on the outside, and usually come in camo green, or khaki. The main design features for this kind of bag are durability and practicality.

Military-style canvas bag

#5 The Saddle Bag

Saddle bags are very similar to satchels, but they’re set apart by the rounded shape of their frontal flap. Originally, this design ingredient was introduced to make the bags easier to wear by horseback riders. Nowadays, it’s just there because it looks cool.

#6 The Multi-Pocket Organizer

If the name of your game is practicality, then you’re best off opting for a multi-pocket messenger bag. Their design was inspired by utility workers, as well as by the bags typically worn by hunters and fishermen. Their outer pockets make it easier than ever to organize and keep your belongings within reach—which makes such a bag ideal for young dads out and about with the young ones.

 #7 The Camera Bag

Still on the practical side, but this time with the pockets on the inside, here’s the camera bag. You don’t necessarily have to be a photographer to wear this style of messenger bag for men. However, you do need to bear its main specific elements in mind. A camera bag will always feature one larger inside compartment, as well as several smaller inner and outer pockets. These were all initially designed to accommodate the various charger and transfer cables that most modern DSLR cameras come with, as well as flashlights, lenses, batteries, and other accoutrements.

What kind of material should you choose for your messenger bag?

 As you can easily glean from the above section, there are three main types of materials used in the production of messenger bags for men:

• * Most messenger bags made of canvas are light- to medium-weight, they’re versatile, as far as style goes, and they are usually inexpensive. Most often, they’re either made of cotton, hemp, or linen. Another plus of going for canvas messenger bags is that they’re easy to care for—simply throw them inside of the washing machine, leave them out to air dry, and sling them back on. Since they’re affordable and come in a virtually limitless array of sizes, designs, colors, and fabric patterns, you might consider building a collection of such bags, to match different outfits for various occasions. Bear in mind that canvas bags are not always water-proof, so check weather conditions, if you plan on transporting a laptop in one.

• * For the best quality messenger bag, definitely spring for leather. Bags made of actual leather can outlast several generations, so don’t be surprised if you find vintage models that have been previously handed down from one generations to the next. Messenger bags for men come in faux leather (or pleather), but also in full-grain leather and suede. One great look to consider is aged leather. In terms of styling, it’s generally recommended to match the shade of brown in which your messenger bag comes with your shoes, belt, and/or watch belt. No need to get too compulsive about it, though, as contemporary rules of style are more lax in this respect.

• * Speaking of pleather: if you’re into protecting the environment, or simply want a highly durable messenger bag that will withstand heavy rain or other poor climate conditions, you can always opt for nylon. Such bags won’t last you a lifetime, since they do tend to get easily scratched, but they are very durable, compared to how affordable they are. Laptop messenger bags usually come in nylon or other synthetic materials, since these are waterproof. Bear in mind that nylon, like all oil-based products, is heat-sensitive. Set the washing machine to the lowest available temperature when cleaning such bags, unless you want them ruined.

 

What’s the best size of messenger bag for men?

There’s never a clear cut answer to such a question, so here are a few things you need to consider, when selecting a specific size of messenger bag:

• * Your height and build. It’s far more important to choose a messenger bag that’s suitable to your particular body shape, then to go for one just because it’s trendy. A good, quick rule of thumb is to always maintain proportions. If you’re short and stocky, go for a medium-sized vertical bag, which won’t make you appear even more diminutive than you already are. You can go for a larger bag if you’re on the tall side, but if you’re rather slim (or lanky, to be completely honest here), don’t choose the biggest bag available. It will make you look even wispier than you already are.

• * Your typical load. Obviously, if you carry your laptop and/or school books with you on most days, you’re going to want to choose a messenger bag than can accommodate them. Most good stores will tell you what the biggest size laptop that can fit in a particular model is. Similarly, a lot of messenger bags come in different sizes—choose the best one for you.

• * Your personal style. If you’re the kind of guy who really doesn’t like to carry around bags, but would rather stuff his belongings into his pockets, don’t delude yourself. You’re not likely to start wearing a bag non-stop, so there’s really no point in buying the biggest and most expensive one available. Find a lightweight bag that you feel comfortable wearing around, when you absolutely have to.

Men’s messenger bags lookbook: 5 styles for your inspiration

1. Urban cool

 

The bag: Vertical, slung back on one shoulder. Sporty design, neutral colors, simple patterning. No outer pockets or unnecessary trimmings.

How to wear it: With your favorite pair of sneakers or Chuck Taylors, a smile, and a hoodie. Pants are not optional, but just about anything goes, from Bermuda shorts to worn-in jeans.

2. Geek chic

 

The bag: Vintage leather satchel. Weathered, with a story. Crammed with art books, text books, and the latest model iPhone/iPad/customized Linux-operated laptop.

How to wear it: With confidence. As far as clothing options go, just make sure everything is clean and (relatively) hole-free. Then feel free to mix and match as you see fit.

3. Office smarts

The bag: Expensive, full-grain heirloom leather briefcase. Contains at least as much money as was paid for it.

How to wear it: With a suit, or at least a blazer. Matching leather goods (wallet, shoes, belt, watch belt) are not mandatory, but will absolutely make the ladies swoon.

4. Artist on-the-go

The bag: Canvas camera/military messenger bag with leather details. Contains about a dozen too many inner pockets, but you never know when you might decide to invest into that ridiculously expensive new lens. You’re rugged, so you’re going to carry it around in a canvas bag.

How to wear it: With at least a 3 o’clock beard. Vest, cap, mountain boots are all optional, but might make you look like you’ve seen some things in your day. Oh, the stories you could tell…

5. Adult casual

 

The bag: A canvas messenger bag that’s practical enough for your dad (i.e., has many pockets), but also hip enough for you to be seen with your dad (i.e., doesn’t have that many pockets).

How to wear it: Shoes, shirt, pants. Improvise at will. If you’re past 50, make sure you don’t go too wild on the whole ‘youthful trends’ thing. Keep it decent and age-appropriate and you might find that your teen/twenty-something actually wants to hang out with you at the mall (or at least will tolerate you, for lack of a better option).