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How to Choose the Right Messenger Bag

Compact yet accommodating, the Vale will expand and contract depending...
Photo: Penney Garrett
Wednesday June 16, 2021
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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 our tested 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 find 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, fewer 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 to and from work in a car or on a train will probably prefer the briefcase-style because they're superior for walking and organizing office essentials while also being more versatile and comfortable than a standard briefcase. If you're on a bike, you will definitely want to prioritize something that is made to ride high up on the back at an angle, free and clear of your bum.

The Especial Stash rose above most of the other bags in our review...
The Especial Stash rose above most of the other bags in our review, in large part due to its thoughtful ergonomics for cycling.
Photo: Penney Garrett

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. You'll want to 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 Burley Transit is great for this scenario, as is the sleek Timbuk2 Especial Stash and the affordable Timbuk2 Classic.

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 requirement, and a cross-body stabilization strap is essential. If you live in a rainy climate, we also suggest choosing a waterproof or weather-resistant bag. Finally, you'll want to seek out a bag with an easily adjustable shoulder strap. It should be easy to adjust with one hand and padded enough to keep your shoulder from getting sore. Additionally, you'll need to be able to tighten this strap quickly, but also lengthen or unclip efficiently to take the bag off.

The iconic seatbelt buckle on the shoulder strap of the Chrome Buran III and Chrome Kadet Sling features an eject button for easy removal. Being able to break apart your shoulder strap with the press of a button means you don't have to pull your bag over your head — potentially losing your glasses and hat, or messing up your hair. The Timbuk2 Especial Stash has a quick-release shoulder strap buckle as well as a completely waterproof laptop sleeve. The Mission Workshop Monty has a fully waterproof laptop pocket too and features an easily adjustable shoulder strap.

The Chrome seatbelt buckle on the Buran III makes getting into and...
The Chrome seatbelt buckle on the Buran III makes getting into and out of your messenger bag easier than any other bag we tested.
Photo: Jared Ross

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. You may want to seek out a bag that can mount onto the trolley handle of your wheeled luggage, so you don't have to wear your bag while dealing with your luggage. 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. Peak Design Everyday Messenger and the Burly Transit both accommodate a trolly handle and would be great for airport travel, owing to their hidden zippered pockets.

The Transit is a great option for travel because it slides onto the...
The Transit is a great option for travel because it slides onto the handle of your wheeled luggage, and has various difficult to access pockets, to ensure your wallet, passport, and phone are difficult to steal.
Photo: Jared Ross

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 Chrome Buran III is an excellent option for students (and professors) with its well-conceived pockets, thickly padded strap, and large padded laptop pocket which can double as a place to stash documents. We also love the Mission Workshop Monty for having a waterproof laptop pocket (though it doesn't have any padding) and tons of space for books, art supplies, or spare clothes in the main compartment. Another solid option to consider is the Arc'teryx Granville — 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. If you're hoping to find something more affordable to commute to campus, we can easily recommend the all-around solid Timbuk2 Classic. It is simple and straightforward, ideal on or off a bike, and it comes in many different sizes and colors. The only drawback to the Classic is that you will want to use a laptop or tablet case, as the laptop pocket doesn't have much padding.

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 bag features are 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. For stealth opening and closing, the Peak Design Everyday Messenger has both a quiet opening/closing mechanism sans velcro and a professional look. Other great options include the classy leather Komal C Buffalo Hunter which is a great option if you aren't a cyclist, or the Especial Stash — which is stealthy and waterproof — if you are.

Another feature you might want to seek out for 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 too. 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 inside. 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 them 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 also 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 or...
Many bags have both a padded sleeve for electronics and a clasp or zipper 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. An ambidextrous strap might be non-negotiable if you're left-handed, as most lefties prefer to carry their messenger bag on their right shoulder.

The Buran has one of the longer padded sections on a shoulder strap...
The Buran has one of the longer padded sections on a shoulder strap in our review. More shoulder coverage means that the weight in your bag is dispersed over a larger area and the strap is more comfortable overall. This shoulder strap is ambidextrous as well - a feature lefties are sure to love.
Photo: Jared Ross

Stabilizing Strap


A stabilizing strap is designed to keep a bag tight on your back for better balance, preventing it from swinging around to the front 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 are often 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 — many companies 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.

The Kadet Sling in "Night" has a reflective panel on the front of...
The Kadet Sling in "Night" has a reflective panel on the front of the bag, to maximize visibility - and safety - when riding at night.
Photo: Jared Ross

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. Some companies have begun to incorporate magnetic buckles and latches. These can be fantastic for eliminating the noise of velcro, but most of these options have a steeper learning curve than their louder cousins.

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

Pockets


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 writing utensils are highly useful as well.

The Everyday Messenger has a plethora of pockets and features for...
The Everyday Messenger has a plethora of pockets and features for dialing in the organization of your daily kit. For some, this could be overkill, but for the right person this could be a storage dream come true. In the case of this bag, the inner dividers are optimized for camera equipment, though they can be creatively used for almost anything.
Photo: Jared Ross

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 best for you.

Many of our friends and colleagues report having gone from a bag, to a pannier, and finally settling on a simple backpack for their bike commutes. As such, the classic "messenger bag" has to triangulate between more essential functions than it did in the past. 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 or walking, to crowded subways or bumpy buses. It's best if it can carry more than just your electronics or work essentials. The best messenger bag should also be able to hold the random essentials of your daily life — like gym clothes, a rain jacket, climbing shoes, or a water bottle.

A messenger bag should be able to carry all your daily essentials...
A messenger bag should be able to carry all your daily essentials, and then some.
Photo: Jared Ross

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 too 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 too. However, many aren't as stylish or waterproof, and they aren't as easy to get into when you're on the go. Many of the companies that make the best messenger bags, also make waterproof commuter backpacks. Chrome, Mission Workshop, and Timbuk2 all have great options to consider. One drawback is that you can't get to your gear as quickly or painlessly as with a messenger bag. Messenger bags let you reach all your items without even taking the bag off your shoulder because you can swing it around to the front. 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


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 a daily basis. They have the capacity for quite a bit of stuff and are particularly great for grabbing 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, because they feel it hampers the nimble-ness of their ride. 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.

Conclusion


We hope this article has helped you narrow down the options and hone in on the right kind of bag and features for your needs. Happy commuting!

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