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How to Choose the Best Messenger Bag

Do you need a messenger bag? What should you look for and consider when choosing one? If you have these or similar questions, keep reading. Our testers used seven different models on daily commutes, international ventures, and miscellaneous adventures. We learned a thing or two about which styles of bags work best in specific scenarios, plus the handiest features. This article highlights whom messenger are for and when they are most useful. We also include our favorite features to look for if you want to get the best bag for your needs.

Two Styles: Messenger & Briefcase

Simply put, a messenger bag is an over-sized purse with a single, cross-body strap. Within this product category, there are two general styles: messenger style and briefcase style. Messenger style bags are best for biking because they sit higher on the back; generally, they have very comfortable straps, large capacities, few pockets, and quick release buckles. Briefcase style bags tend to have semi-rigid back panels, many storage options for small items, built-in laptop sleeves, and top grab handles. Their straps are designed for walking and they are most comfortable sitting lower on the hip or low back.

All messenger bags can be worn while biking or while walking but not all are best for either activity.

The easiest way to tell the difference between the two is to look at the strap design. Vertically oriented straps, some of which are removable, are best for walking, while angled straps are meant for biking. The former will position the bag more like a purse near your waist and the latter will sit nearly vertical and high on your back. The average American who goes directly to and from work will prefer a briefcase style because they're superior for walking and organizing office essentials and more versatile and comfortable than carrying a briefcase.

The Mini Metro bag from Chrome is a stylish bag optimized for use on the bike with an angled shoulder strap.
The Mini Metro bag from Chrome is a stylish bag optimized for use on the bike with an angled shoulder strap.

Five Use Scenarios

Moving on from how these bags work for walking vs. biking, the next question you should ask yourself is what you plan on putting in your bag. Below, we outline a few different ways we liked to use these bags and our recommendations on things to consider for each use. We also point out which bags stand out above the rest for certain applications thanks to their unique features.

The Mobile Desk

While writing this review, we used the products as mobile office organizers. If you work remotely and frequent libraries and coffee shops, then a messenger is a great choice for you. Pick a bag that has the organizational capacity for all your things. It's not just about carrying your stuff from point A to point B, your things should also be accessible when your bag is on the ground beside you. Get a bag that has a laptop sleeve. Otherwise, you'll need an after-market laptop sleeve, which tends to be a less efficient use of space than an integrated sleeve. We also prefer bags that have pockets big enough for a power supply. Pen/pencil slots are a must. Another thing to look for in a mobile office bag is the ability to keep papers from wrinkling like separate document pockets. The Osprey FlapJack Courier is a great mobile office bag and has an internal grab loop that makes moving to a new workspace a breeze. We also like the Mobile Edge ECO for this purpose.

Mobile office features of the Classic - Top Left: Napoleon pocket. TR: zipped pocked  key clip  and open pocket. BL: Internal compartment pockets and organizer  BR: internal compartment and rear laptop pouch.
Mobile office features of the Classic - Top Left: Napoleon pocket. TR: zipped pocked, key clip, and open pocket. BL: Internal compartment pockets and organizer, BR: internal compartment and rear laptop pouch.

The Bike Commuter

Fourteen-mile bike commute? No problem. You want a bag that will carry your stuff plain and simple. You may not need extra organizational features or fancy laptop sleeves. We suggest prioritizing a bag that's comfortable and carries well. If you live in a rainy climate, we also suggest choosing a bag that is waterproof. If you live in California, this won't be as much of an issue. The ease of adjustment of the shoulder strap is a huge feature for the long distance bike commuter. You want a strap that can be adjusted one-handed and is padded well enough to keep your shoulder from getting sore. You need to be able to tighten the strap quickly, but you also need to be able to lengthen or unclip the strap to take the bag off. The Chrome bags feature an eject button that makes taking the bag off almost too easy.

Biker commuters should look for shoulder and stabilizing straps that secure the bag high and tight on your back. The best shoulder straps for biking are asymmetrical and let the bag ride a few degrees off vertical.

If you're a bike commuter, seek out a great stabilization strap. There are two main designs: those that clip to the shoulder strap perpendicularly (T-strap) and those that are worn across the body like a hip belt. The best design depends on your personal preference. On one hand, we love the hip belt style because it keeps bags secure and takes some of the weight off the shoulder. However, some people find anything around their waist uncomfortable for biking long distances. If that's you, go for a T-strap. Several bags we tested can have stabilizing straps that can be used either way. The Timbuk2 Classic is a solid example.

The Classic from Timbuk2 plays well with bike commuters.
The Classic from Timbuk2 plays well with bike commuters.

The other important aspect of messenger bags designed for biking is the fit against your back. Visualize someone hunched over while riding a bike and notice how their back is somewhat curved. Now picture strapping a flat piece of plywood to their back. One of two things happens, either the person's back straightens or the board rests against the person's shoulder blades and one or two unfortunate vertebrae. Either scenario will be quite uncomfortable for our imaginary commuter. Replace the board with a laptop and the straps with a messenger bag and you can see why some models aren't that comfortable for biking. Good choices for biking have flexible back panels that contour to a rider's back, or they have substantial padding (for the sake of protecting your laptop and your back). If you don't carry rigid objects like laptops, this won't be an issue for you.

The Traveler

Head to any airport and you'll see folks with messenger bags as their "personal item." If you plan on traveling with your bag, focus on durability, style, good organization, and laptop/tablet protection. For more security, stabilizing straps make a bag more difficult to steal and minimal external pockets help reduce pick-pocket opportunities. Flaps that are difficult to open are nice too. Some bags we tested have secret pockets for keeping money or a passport safe. The Tom Bihn Daylight Briefcase is compact and convenient for airport travel. If you opt for the integrated cache to protect your tablet or Chromebook, you get excellent laptop protection in a TSA friendly compartment. This reduces the hassle of removing your laptop for security, as well as the chances of you dropping your laptop or forgetting it at security checkpoints.

The cache of the Tom Bihn bag flips out of the messenger. This means you don't have to remove your laptop completely at TSA checkpoints.
The cache of the Tom Bihn bag flips out of the messenger. This means you don't have to remove your laptop completely at TSA checkpoints.

The Student

Carry a heavy load of school books every day? You're going to want a bag with max storage space and max comfort. You'll also benefit from a laptop compartment and a place to keep papers safe from wrinkling. The Patagonia Black Hole is a great pick. It works well on and off a bike, and is one of the most water resistant bags in this review. It is lightweight and spacious enough to fit the essentials for a day of classes. Its superior style will also score you points across campus, especially in the eco-conscious crowd.

The Black Hole easily swallows up laptops  books  and most any school supplies one might need during a typical day on campus.
The Black Hole easily swallows up laptops, books, and most any school supplies one might need during a typical day on campus.

The Professional

You're on your way to work to present your proposal to upper management at the end of the first quarter strategy meeting. But you get a flat on the way and are now running ten minutes late. You sneak into the meeting right as the presenter makes a joke that has everyone laughing, and no one notices you - success! You open your bag with the loud rip of the flap velcro just as the room gets quite; all of a sudden, all eyes are on you. Ok, that might be a little extreme, but it's situations like this that make features like Velcro silencer strips a superb addition to messenger bags used in professional business environments.

Another feature you'll want to look for is a comfy carry handle so you can use your bag like a briefcase while walking around the office. If you like hitting the gym over lunch, extra space is also nice so you can bring an extra change of clothes. This is also nice when you want to pick up groceries on the way home. You'll probably want some laptop protection and a good place for papers as well.

Don't forget style. Flashy colors are fun, but more a more subtle look tends to be preferred in management. If all this sounds like what you're looking for, consider the Timbuk2 Proof that has quiet buckles, good laptop protection, and has a more sophisticated look (for a messenger, that is).

The Proof from Timbuk2 keeps it classy with neutral looks that look pleasant without stealing attention.
The Proof from Timbuk2 keeps it classy with neutral looks that look pleasant without stealing attention.

Features to Consider

Water Resistance

Relatively speaking, it's easy to make a waterproof bag. If the flap is made with a waterproof fabric, the only place water can enter is the fold at either edge of the flap. Most of the products we tested include wings that cover this gap. The most weather resistant bags tout completely waterproof fabrics and generous corner wings. When the bag is cinched properly, it will be impossible for rain to enter the bag. When you're purchasing your bag, be sure that the flap will cinch down on your belongings and that the wings look as though they will funnel water out, not in. Finally, keep in mind that external pockets are more difficult to protect.

In part because most of the products in this review are not dunk proof, manufacturers label the bags as water resistant rather than waterproof.

The Edge ECO kept its contents dry in our OGL Weather Test.
The Edge ECO kept its contents dry in our OGL Weather Test.

Laptop Protection

If you want to use your new purchase bag to carry around a laptop, you'll want to look for a bag that has a protective laptop compartment. Moreover, floating laptop compartments that are sewn to a rigid or semi-rigid back panel will keep your laptop completely off the ground and are highly recommended. Thick padding all around the compartment will also protect it against accidental falls on the sides of the bag.

Shoulder Strap

Shoulder strap padding and design are important. Decide if you're primarily going to use your bag for walking or biking. Straps that have more padding are typically more comfortable, but factors like adjustability are also important to consider. Some straps are designed to be set once and are difficult to adjust on the go. Others are tightened or loosened with one hand. Bags that have ultra adjustable straps usually favor one shoulder. Some of our testers loved being able to switch the bag between the left and right shoulders, while others were creatures of habit.

The should strap adjusting mechanism of the Classic.
The Timbuk2 Classic messenger bag.

Stabilizing Strap

A stabilizing strap is designed to keep the bag from swinging around while you're biking and to keep the bag tight on your back for better balance. Many people opt out of using stabilizer straps when walking. These straps either connect across your hips or stomach like a backpack's hip belt or they connect to the shoulder strap and go under your arm like a "T". Horizontal straps take a bit of the weight off your shoulder and can often be more comfortable. When riding a bike, however, many people don't like having anything around their waist and are more comfortable with T-strap designs.

Reflective Patches

Before dawn or after dusk, you'll want to do everything you can so that cars see you. Most bag manufacturers include some reflective material on the back of the bag. If your plan is to ride in the dark often, you should definitely make use of the bike light attachment points that most bags have. The style is the biggest thing that suffers when there are a lot of reflective strips.

Nighttime riding isn't the time to be stealthy, so a healthy dose of reflective material is always welcome.

Flap Closure

Most flaps have a two-part closure system using some type of Velcro and a clip of some sort. The most common design uses plastic buckles. These are simple, quick, and intuitive. One negative aspect: plastic buckles are difficult to use one-handed while the bag is on your shoulder. If you frequent crowded areas, be careful of pickpockets who can easily unclip them and steal your stuff. Hooks are another flap closure that we saw. While hooks are fast to use, they also make it easy to open the main compartment even while wearing the bag. Again, these would be super easy for a thief to get into.

Most bags also have Velcro strips. When traveling short distances, we often forwent clipping the buckles or hooks and relied solely on the Velcro. If you're sneaking into a meeting, the screech of ripped Velcro can be an unwanted attention grabber. Because of this, some bags have Velcro silencer strips.

The Proof doesn't use Velcro  instead relying on a simple and unique closure system to keep the flap in place.
The Proof doesn't use Velcro, instead relying on a simple and unique closure system to keep the flap in place.


Messenger bags can be as simple as one main compartment or they can have pockets in all shapes and sizes. The pockets you need will depend on your use and the stuff you like to carry. Our favorite bags had a range of pocket sizes and shapes. For example, flap pockets are a nice place to store small items like keys. Back pouches make a great place to keep papers safe. As a general organizational rule, anything smaller than the size of a baseball is best kept in a pocket rather than the main compartment.

The Mountain Briefcase brings solid organization with a variety of pocket shapes and sizes  all placed in convenient and efficient places.
The Mountain Briefcase brings solid organization with a variety of pocket shapes and sizes, all placed in convenient and efficient places.

Messenger Bag Alternatives

Messenger bags are a great addition to your bag line-up because they provide quick access to your stuff, are ultra-portable, can take a beating, and are typically much more water resistant than other bags. Some are quite stylish, too. They are, however, neither as comfortable as most backpacks nor can they carry as much stuff. They cost more on average than laptop bags and are heavier than purses, too. It's best to think about what you carry around on a daily basis, how you get to work, what role aesthetics and style play in your purchasing decisions, how quickly you need to access the contents of your bag, and the weight of what you carry before deciding what type of bag or pack is right for you.

Many of our colleagues report having gone from bag, to pannier, and finally settling on a simple backpack for their bike commutes. As such, we believe that the classic "messenger bag" has bigger shoes to fill in the modern world. It's a casual briefcase for reluctant business people; it needs to be comfortable for a variety of commuting methods, from cycling to walking to crowded subways, and bumpy buses; and it often needs to hold a few other random items like gym clothes, rain jackets, climbing shoes, etc.

Keeping up with the times  the Topo Designs bag switches seamlessly between messenger bag  backpack  and briefcase.
Keeping up with the times, the Topo Designs bag switches seamlessly between messenger bag, backpack, and briefcase.

We see the messenger bag being supplanted by backpacks for many urban bike commuters, and in turn, the messenger bag seems to be replacing the formal briefcase—likely for the casual style and the increased carrying comfort (a softer-sided bag is nicer to carry and handle). We liked to use our bags as a carry-on or "personal item" on flights for their carrying comfort, and how easy it is to quickly stash essential items or pull things out in a crowded airport.

If a messenger bag doesn't fit your lifestyle but you are still seeking optimal carrying power in some form of bag or sack, here are some alternatives that might suit you better.

Laptop Backpacks

Laptop backpacks are the most popular substitutes for bags. Typically, they are more comfortable, especially for longer distances, and often carry more stuff. However, they aren't as stylish or waterproof, and they aren't as easy to get into on the go. Messenger bags let you reach all your items without even taking the bag off your shoulder. Because they cover less surface area on your back, they also keep your back dry on hot summer commutes. 

Probably the biggest reason to choose one over the other comes down to your priorities and personal preferences. Do you value comfort and capacity or quick access and style? If you commute long distances, you'll probably prefer a backpack. If you just use your bag to carry your laptop around, you'll probably do better buying a messenger bag.

Laptop Bags

The Case Logic 17.3-Inch Laptop Case is much cheaper than a messenger bag and has most of the same functionality.
If you're buying a bag primarily to carry your laptop, keep in mind there are some laptop bags for under $30 that may serve your needs well for a lot less money. Although laptop bags may not be as waterproof, durable or stylish, they usually offer more laptop protection than messengers. They are also lightweight, slide under an airplane seat easily, and provide immediate access to your most reached for items. They usually fit in a waterproof backpack or bag, which gives you even more protection. See our article on our favorite mobile office setup. 

Want the protection of a laptop bag, but the style and features of a messenger bag? You can always purchase an inexpensive laptop sleeve! Laptop sleeves are a fantastic and cheap way to keep your laptop safe in any bag, and some companies even make them fit and attach inside your messenger bag.


Panniers are saddlebags for your bike; although cyclists on bike tours frequently use them, they are also a fantastic way to carry your things on an everyday basis. They have the capacity for quite a bit of stuff and are particularly great for groceries. In the summer, you'll stay much drier keeping the load on the bike and off your back. Panniers aren't as versatile because they are harder to carry around when not riding. Also, some people don't like the feeling of added weight on their bikes, citing reduced mobility. If this isn't an issue for you and you don't need to walk far once you reach your destination, panniers are tough to beat.

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