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How to Choose the Right Messenger Bag

Photo: Penney Garrett
Wednesday January 15, 2020
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Searching for the perfect messenger bag? Curious about various detail and design considerations to consider when choosing one? Our testers used 13 different models on daily commutes, international escapades, and miscellaneous adventures. They learned a thing or two about which styles work best in specific scenarios and identified the handiest features. This article highlights who messenger bags are for and when they are most useful. We also discuss our favorite features so you can end up with the best bag for your needs.

Two Styles: Messenger & Briefcase

In its simplest form, a messenger bag is an oversized 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 that being said, bags in this category become more and more innovative and creative each year, blurring these lines considerably.

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

The easiest way to tell if a bag will be best for walking or biking 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 closer to vertical and high on your back. The average person that goes directly to and from work will probably prefer a briefcase-style because they're superior for walking and organizing office essentials while also being more versatile and comfortable than a standard briefcase.

This stylish bag is optimized for use on the bike, thanks to an...
This stylish bag is optimized for use on the bike, thanks to an angled shoulder strap.
Photo: Lyra Pierotti

Five Use Scenarios

The next question you should ask yourself is what you plan to put in your bag. Below, we outline different ways we use these bags and recommendations to consider for each use. We also point out which models stand out above the rest for certain applications, thanks to their unique features.

The Mobile Desk

While writing this review, we used our bags as mobile office organizers. If you work remotely and frequent libraries and coffee shops, a messenger is an excellent 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 belongings should also be accessible when your bag is on the ground beside you. Getting a bag that has a laptop sleeve is highly recommended. 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 for some folks. Another thing to look for in a mobile office bag is the ability to keep papers from wrinkling with features like separate document pockets. The Topo Designs Messenger Bag is great for this scenario, as is the tried-and-true Timbuk2 Classic and the wildly affordable Mobile Edge ECO.

Mobile office features of the Timbuk2 Classic - Top Left: Napoleon...
Mobile office features of the Timbuk2 Classic - Top Left: Napoleon pocket. TR: zipped pocket, key clip, and open pocket. BL: Internal compartment pockets and organizer. BR: internal compartment and rear laptop pouch.
Photo: Jeremy Bauman

The Bike Commuter

Fourteen-mile bike commute? No problem; you'll likely want a bag that facilitates comfort and security while on the move. Whether or not extra organizational features or a fancy laptop sleeve are things you need, something ergonomic that carries weight well is a sure requirement, and a cross-body stabilization strap is essential. If you live in a rainy climate, we also suggest choosing a waterproof bag. Finally, the ease of adjustment of the shoulder strap must be on point. You want to look for something that can be adjusted one-handed and is padded enough to keep your shoulder from getting sore.

You need to be able to tighten it quickly, but also lengthen or unclip efficiently to take the bag off. The seatbelt buckle on the strap of the iconic Chrome Mini Metro features an eject button and has become a fan favorite. The Timbuk2 Especial Stash, our Editors' Choice, has a quick-release buckle as well as a completely waterproof laptop sleeve. Both the slim and low-profile Chrome Vale 2.0 and the Timbuk2 Classic also have straps that slide open and secure tightly with ease.

The angled and padded shoulder strap and stabilization strap of the...
The angled and padded shoulder strap and stabilization strap of the Especial Stash mean your belongings will be comfortable and secure your entire commute.
Photo: Penney Garrett

Bike 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.

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 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 books or a computer, this will be less of an issue for you.

The padded and moldable back panel of the Arc'teryx Granville helps...
The padded and moldable back panel of the Arc'teryx Granville helps it be a very comfortable bag for cycling.
Photo: Penney Garrett

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, 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...
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.
Photo: Lyra Pierotti

The Student

Carry a heavy load of school books every day? You're going to want a bag with max storage space and comfort. You'll also benefit from a laptop compartment and a place to keep papers safe from wrinkling. The Topo Designs Messenger Bag is a great choice for this with its well-conceived pockets and thickly-padded strap. Another solid option to consider is the Arc'teryx Granville 10 — it works well both on and off a bike and is highly water-resistant. We tested the 10-liter size, which is likely a bit small for most students, but you can also purchase it in the 16-liter size for not much more. The same goes for the all-around solid Timbuk2 Classic — simple and straightforward, it's ideal on or off a bike and comes in many different sizes and colors.

Even with the smaller 10-liter version of the Granville we were able...
Even with the smaller 10-liter version of the Granville we were able to fit quite the load of school necessities: laptop, papers, books, and - most importantly - a mug for coffee!
Photo: Penney Garrett

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 tire 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 then open your bag with the loud rip of the Velcro flap just as the room gets quiet; all of a sudden, all eyes are on you. Situations like this illustrate why considering all use cases and the features a bag offers is so important. Things like Velcro silencer strips are a superb addition to messenger bags used in professional business environments. Or, search out a bag that has buckles and zippers instead of velcro for an even more straightforward solution. The classy leather Komal C Buffalo Hunter is a great option here if you aren't a cyclist, and the Especial Stash is stealthy and waterproof if you are.

Another feature you might want to look for in a career-minded bag is a comfy carry handle so you can use it as a briefcase when walking around the office. If you enjoy hitting the gym over lunch, extra space for a change of clothes is nice. Roominess is also essential if you want to be able to pick up groceries on the way home after a long day. You'll probably want some laptop protection and a good place for papers as well. Finally, don't forget style. Flashy colors are fun, but a more subtle look tends to be preferred in professional environments.

If you don't need technical features meant for cycling or inclement...
If you don't need technical features meant for cycling or inclement weather, consider something classic and business-savvy like the Buffalo Hunter.
Photo: Penney Garrett

Features to Consider

Water Resistance

It's easy to make a waterproof bag — just use waterproof materials, yes? While the right fabric and lamination go a long way, there are a few other things to consider. If there's a flap, look for wings that cover the fold at either edge where moisture might be able to sneak. Make sure that these wings will funnel water out, not in. Most of the products we tested include this design feature, and when the bag is cinched properly, the inner compartments will be pretty impervious to rain. Next, assess the external pockets as these can be a weak point, especially if the zippers themselves aren't waterproof — another thing to look for. Waterproof zippers will be coated, covered, and have smaller teeth that are far less exposed. Finally, you will want to take note of stitching and seams. Taped seams are a great indicator that the manufacturer took care to keep water out at every point.

Because messenger bags are not dunk-proof dry bags, manufacturers label the bags as water-resistant rather than waterproof.

The Especial Stash is highly weather resistant and even offers a...
The Especial Stash is highly weather resistant and even offers a fully-waterproof padded laptop sleeve. If you live in a rainy climate, this is the bag you want.
Photo: Penney Garrett

Laptop Protection

If you want to use your bag to carry around a laptop, be sure it has a protective compartment designed for that purpose or that there is enough room for your computer to fit when inside its own case. Going case or padding-free is not ideal for obvious reasons. 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.

Many bags have both a padded sleeve for electronics and a clasp to...
Many bags have both a padded sleeve for electronics and a clasp to further ensure that your valuable gadgets stay safe and secure.
Photo: Lyra Pierotti

Shoulder Strap

Shoulder strap padding and design are important, and you'll want to 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 made to be 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 shoulder strap adjusting mechanism of the Timbuk2 Classic is...
The shoulder strap adjusting mechanism of the Timbuk2 Classic is made with the intent of allowing quick adjustments without having to deal with a bunch of excess webbing.
Photo: Lyra Pierotti

Stabilizing Strap

A stabilizing strap is designed to keep a bag tight on your back for better balance, disallowing it from swinging around while you're biking. Many people opt out of using stabilizer straps when walking. These straps either connect horizontally 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 a T-strap design.

A stabilizing strap under the armpit is a pretty essential feature...
A stabilizing strap under the armpit is a pretty essential feature for bag security while biking.
Photo: Penney Garrett

Reflective Patches

Before dawn or after dusk, you'll want to do everything you can so that cars see you. Most manufacturers include some reflective material on the back of their bags, but if you plan to ride in the dark often, you should also plan to use bike lights — most bags also offer light attachment points for this purpose. Style is the biggest thing that suffers when there are a lot of reflective strips, but if you're biking every day, it is a small price to pay for safety.

Even small reflective strips can make a big difference, though the...
Even small reflective strips can make a big difference, though the more the merrier if you bike at night regularly. Flashing lights are also highly recommended.
Photo: Penney Garrett

Flap Closure

Bags with flaps often have a two-part closure system using Velcro and a clip of some sort. The most common design uses plastic buckles, which are simple, quick, and intuitive. Hooks also get used sometimes and can be more durable as they're frequently made from metal instead of plastic. Keep in mind that Velcro is loud to open and close — depending on your profession, it may not be the best choice. Bag companies are always experimenting with alternate designs and closure systems; just be sure to consider both ease of use and security.

The magnetic clip on the flap of the Especial Stash is super easy to...
The magnetic clip on the flap of the Especial Stash is super easy to use - even one-handed. The flap is also Velcro-free so you can open your bag in quiet places without making hardly a sound.
Photo: Penney Garrett


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. If you don't carry your own separate pencil bag, then slots for pens are highly useful as well.

The Topo Designs Messenger is the only bag in our review to offer a...
The Topo Designs Messenger is the only bag in our review to offer a full-sized pocket on the underside of the front flap.
Photo: Penney Garrett

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, not 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. 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 may need to be a casual briefcase for a reluctant business person or a do-it-all mobile office for a remote worker or student. It needs to be comfortable for a variety of commuting methods, from cycling to walking to crowded subways, and bumpy buses. And it's best if it can hold a few other random items like gym clothes, a rain jacket, climbing shoes, or a water bottle.

To keep up with the changing desires of commuters, companies like...
To keep up with the changing desires of commuters, companies like Timbuk2 are making more hybrid and convertible bags. Here you can see the Mission Sling getting used both across the shoulder and as a fanny pack. It's not a big bag, but it's mighty in what it can offer!
Photo: Penney Garrett

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. This is likely for the casual style and increased carrying comfort they can offer — 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 because they are comfortable to carry and also easy 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 messenger bags. Typically, they are more comfortable, especially for long distances, and usually, they can hold more stuff. However, many 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, it's also easier for your back to stay 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...
If you're buying a bag primarily to carry your laptop, keep in mind some laptop bags for under $30 may serve your needs well for a lot less money than a messenger. Although laptop bags may not be as waterproof, durable, or stylish, they usually offer more laptop protection. They are also lightweight, slide under an airplane seat easily, and provide immediate access to your most reached for items.

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 to 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 cooler and 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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