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Getting to grips with the messenger bag


For men, a messenger bag is the ideal companion. If you’re thinking about purchasing a versatile, well-sized bag that looks smart and sleek, then a leather messenger bag will tick all of your boxes.

Of course, you may want to consider other varieties of bags as well, so why not check out our article on different types of bags for men, if this is the case.

Messenger bags are just as practical for day-to-day use as they are at the weekend. If you’ve never owned one before, or you’d like to learn more about what is a messenger bag, this piece will detail everything you need to know. 

What is a messenger bag?

The messenger bag first became widely popular as a practical fashion item back in the 1990s (although the style dates back to the mid-19th century) and not just with men either, plenty of women loved their minimalistic style and versatility. Generally, the style of messenger bags has remained relatively simple, and, over the past ten years, they have become a real style icon.

A messenger bag is a rectangular receptacle that features a wide shoulder strap that’s comfortable to wear, and a sizeable flap with a clasp or buckle to keep your belongings safely stored away in the main interior compartment. Many are wider rather than taller.

Today, these types of bags are the go-to for so many different types of men, whether you’re a student, work in the city or you’re more of a marketing guru – perhaps you just need something that keeps your belongings safely tucked away? Comfortable to wear and generally lightweight, these bags slip across the body or on the shoulder. For those of you that carry laptops, choosing a wide messenger bag will suit you well, and if you have other paraphernalia that you like to take to work with you every day (pens, water bottles, perhaps an iPad?), simply choose a roomier version.

There’s lots of choice out there, from canvas to sturdy leather, even vegan leather and nylon options. One thing that messenger bags usually have in common is that they’re hard-wearing. As well as the body material, if you’re looking for a quality piece, take note of hardware, such as the closure mechanism for sturdiness, the adjustability of the straps to ensure a snug fit and the quality of the interior lining.

Open brown messenger bag with books and laptop inside

Benefits of the messenger bag

So, why a messenger bag? Well, it makes a great gift, it’s the ideal work-bag and a weekend staple. A leather messenger bag is the practical choice for today’s well-turned-out man. They’re also very much in fashion at the moment and the trend is for that to continue. Owning a messenger bag will give you years of good use, especially if you choose one constructed out of premium materials.

Here are a few key benefits associated with the messenger bag:


They’re usually spacious, and a well-made messenger bag should feature a variety of compartments and pockets, keeping you well organised at all times. Use these to store away pens, your phone, tablet, keys and more. If you want to take your laptop with you to the office, choose a larger size messenger bag with a quality lining.


The materials involved are often strong and durable, meaning messenger bags can cope with the demands of contemporary living.


The shoulder strap should be comfortable to wear, wide enough to carry a laptop and ergonomically designed to sit well on your shoulder or across your back.


A messenger bag is the ideal in-between bag that gives you lots of flexibility. You can wear it for work because it looks professional but you can also wear it at the weekend as it has that hybrid appeal. It is generally smarter than a backpack and less formal than a briefcase.


For the style-conscious man, these bags make a statement. You'll want a messenger bag with a simple silhouette that pairs style with practicality. 

Clever design

When you need to reach for something quickly, the compartments make it easy to access it. No more rummaging around looking for that spare biro that’s somewhere at the bottom of your backpack…

Navy leather messenger bag worn by a man over his shoulder

Disadvantages of the messenger bag

A messenger bag isn’t for everyone and here’s why it might not be the best fit for you.

Messenger bag vs backpack debate

If you do carry a heavy load regularly, then a messenger bag might not fit everything you need in it and can become uncomfortable. You might be better suited to a backpack instead, which distributes the weight evenly. A messenger bag is designed to cross the body or wear on one-shoulder rather than on the back. So that padded, wide strap is essential for providing user comfort.

Poorly equipped for sustained travel 

If you travel regularly and for a sustained amount of time, then go back to that backpack. That said, a smaller messenger bag is excellent for keeping your travel documents safely stored away while being easily accessible too. For more tips on what to pack for travelling, click here.

Messenger bag vs briefcase debate

You could argue that a modern briefcase is more sophisticated than a messenger bag; this is subjective and depends on your own personal style.

History of the messenger bag

The messenger bag has an interesting history dating back to 1860s America, when Buffalo Bill, the most famous Pony Express rider of all, wore one while riding. The name ‘messenger bag’ actually comes from the aforementioned Pony Express, which was an American mail delivery service that used horse-mounted riders to distribute post, specifically between Missouri and California.

During the 1950s, thanks to the De Martini Globe Canvas Company, it transformed into a bag similar in style to today’s version, especially for line workers and postal workers. These were made out of cotton canvas with a waterproof lining. Strong and durable with plenty of space, they were designed to carry heavy tools; the bags also featured pockets and straps for easy closure. The original bag is still available to buy today.

In the 1960s bicycle messengers, couriers and more postal workers started using the bags to deliver messages and mail and the idea caught on. Over the following 20 years, the messenger bag morphed and became available in other colours, as requested by the companies that used them. 

The next phase was bringing the bag into fashion and that was done by a gentleman called John Peters in the mid-1980s, who updated the bag and made it a fashion icon. His bags included light-reflective strips, binding and buckles, and were made from nylon.

The bag grew in popularity and was a fashion staple seen on university students who carried it into their working life later on. Today, it’s an urban fashion accessory that is often associated with hipsters. While hipsters still favour the messenger bag, it’s definitely a bag coveted by men in all walks of life. Remember Jim Halpert in the US version of The Office? He was always wearing a messenger bag.

Painting of a Pony Express rider featuring an early messenger bag

How to wear a messenger bag

You’re ready to buy a messenger bag and obviously, you want to wear it properly, for practical reasons as well as style.

Not to be confused with the satchel, a messenger bag is ergonomically designed to rest at the side of your body due to its wide strap, which is made with comfort in mind. It can also be worn across the body against the lower back. The idea here is that you reach for your bag when you need to take something out. Satchels traditionally have longer shoulder straps than messenger bags, so can be worn on the shoulder, sitting on the hip, as well as across the body.

The messenger bag is so versatile, it can be worn with your favourite business wear, whether it’s a smart suit or a blazer with jeans. On the weekend, pair it with smart-casual attire for a more relaxed look.

Man holding brown leather messenger bag

Different types of messenger bags

There’s many different types of messenger bags available, let’s consider five key examples here:

  • Satchel messenger bag
  • Briefcase messenger bag
  • Vertical messenger bag
  • Military messenger bag
  • Saddle messenger bag

The satchel messenger is similar to a satchel in that it has two vertical straps that fasten the bag. These are usually attached to the flap that closes the bag. While the briefcase messenger is made of leather and features a front flap. Sometimes there are two straps with a buckle and an outer pocket or two.

The vertical messenger bag is a taller, narrower version of a messenger bag. Then there’s the military messenger, a heavy-duty style option, often made out of canvas. Roomy and with plenty of compartments, you’ll find these come in earthy tones such as khaki, grey and brown. Finally, there’s the saddle messenger, which is similar in design to a satchel, with a round flap area. You’ll often find these made out of leather or canvas.

Man styling a blue leather messenger bag


So now you’re aware of the key benefits and disadvantages associated with the messenger bag, as well as the bag’s celebrated history. Is it time to add this classic receptacle to your everyday wardrobe?

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    • What is a messenger bag?

      It is a useful men's cross-body or shoulder bag that features a large, comfortable strap, a front flap with fastening and plenty of compartments inside to store your personal items. It is usually made out of hard-wearing materials such as leather, canvas, nylon, or vegan leather.

    • How to wear a messenger bag?

      Wondering how high to wear a messenger bag? This type of bag is designed to be worn cross-body with the main area sitting on the hip or just around the back. Alternatively, it can be worn on the shoulder.

    • Is a messenger bag better than a backpack?

      This depends on what you want to use yours for. If you’re planning on carrying a lot with you and have a heavy load, then a backpack is likely to be more comfortable. A messenger bag has useful compartments that make it easy to find what you want quickly. It’s also designed to carry essentials such as a laptop, smart phone, tablet and documents. A backpack is better for cycling because it is worn on the back.

    • How do you use a messenger bag?

      A messenger has so many different practicalities. It’s great for work use as it has plenty of storage inside.For students a generously sized messenger carries notebooks, tablets, study books and laptops and for travelling it’s the perfect accessory to keep all of your travel documents nicely stored away yet easy to find when you need them. And if you’re wondering: are messenger bags cool? The answer to that is undoubtedly, yes.

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