10 Best Waterproof Messenger Bags in Canada for 2023

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We review the best waterproofed messenger bags available on the current market, that will keep your valuables bone dry during commute.

Once an essential carry bag used only by couriers, messenger bags have now become a huge part of men’s fashion. Women’s messenger style luggage is also rising in popularity, but waterproof messenger bags for men have become a staple for many.

Typically used as a laptop bag, they are best known for their rugged canvas or leather exterior with a vintage touch of buckles and straps. New and upcoming designs feature different takes on the traditional materials, giving an updated look and feel.

Also known as bike messenger bags, the classic styles are worn over the shoulder and chest, resting on the lower back or in front. They are loved for their convenience, as you can carry everything around in a stylish way that is also comfy on the shoulders.

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Why Should I Use a Waterproof Messenger Bag?

Well, carrying around your expensive valuables can be tricky business when the weather takes a turn.

Imagine it starts raining or hailing, or a car is heading for that huge puddle in front of you, or you’re standing next to a fountain with tons of backsplash – you can be exposed to moisture at any time of the day. With an impermeable bag, you can keep everything safe and dry in any weather.

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Since there is such a massive amount of designs and colors on the market, it is hard to find the right one, and backpacks that are used for travel aren’t always ideal for best protecting, specifically, our laptops.

If you’re pondering where you even begin to understand the benefits of the new modernized features, well, that’s where we come in. With our in-depth list of the best waterproof messenger bags to guide you to the top models on the market, while comparing their specifications against lesser models. We also show you the main aspects and features of a good waterproof messenger bag for prospective buyers.

10 Best Waterproof Messenger Bags in Canada to Buy Online

1. Timbuk2 Classic Messenger Bag

One of the best sellers, this is like a twist on the iconic courier style. The twist comes from the materials, as it’s made from a mix of polyethylene (PE) and vinyl acetate all from Cordura, unlike canvas or leather models. Both the exterior and interior are waterproof, with an added impermeable TPU inner lining for further protection. Something to note though is to make sure that you close the flap properly using the integrated ear design, otherwise water can get through the corners.

Another contemporary twist is the partially hidden front buckles. This was done to clean the outline of the bag, giving a more sophisticated look. Integrated compression straps let you manage the space inside, as you can cinch them and compress everything for a neater fit.

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When you don’t have time to throw the whole thing over your shoulder, the low-profile grab handle on the back lets you pick it up quickly. When using the shoulder element, you’ve got an added cross strap when riding your bike. Plus, the patented double-loop CAM buckle adjusts rapidly with one hand.

Let’s break down organization. The front flap opens and closes with 2 simple buckles and a strong Velcro attachment. A front zippered pouch has an embedded key strap, and within this you have a stash pocket, and Napoleon pocket to hide keys, wallet, and phone.

You can access this Napoleon pouch without opening the main flap. Inside, 2 stretch pockets safely keep bottles or electronics. A slash pocket separates the main section into 2 parts, great for keeping papers or books. Against the front there is a simplified organizer with several open pockets, plus a big zippered pouch for other loose bits and bobs.

Note: Check out our other page for a full Timbuk2 Messenger Bag Review, for a look at many other models in their line.

Key Features:

Extremely Waterproof TPU Lining Adds Protection
Highly Organized 10 Pocket Options
Available in 4 Sizes in Various Patterns

2. BRASS TACKS Leathercraft Vintage Messenger Bag

The inherently vintage look and versatile design of this bag from Brass Tacks Leathercraft makes it a hit with both men and women. With a rugged waxed canvas exterior, this also features a highly durable horse leather trim. The canvas has a tight double-knit weave, which creates further defense against moisture. It’s hard-wearing, resistant to scratches or color fading.

The large capacity design makes it ideal for all kinds of office supplies and all other necessities. The convertible feature comes from the backpack straps, so you can opt to carry it on your back for a higher level of comfort. You can use one of the straps for over-the-shoulder carrying, plus there are 2 other handles.

The dedicated device pouch has a padded sleeve to protect laptops and tablets, keeping them locked in., You’ll find multiple pockets for storing all kinds of items, and the main section is the perfect size for standard A4 notebooks and papers. As well as various interior pouches, there are 2 external pockets hidden behind the flap, and 1 behind.

We especially love the external pouch that comes out of the bag when it’s closed, so you can fit much larger items like an umbrella, badminton rackets, or other larger supplies. It greatly increases the amount of space, so you can take more items with you.

Key Features:

Highly Waterproof Oil Waxed Canvas & Crazy Horse Leather
Very Secure with Zippered Closure Under Main Flap
USB Charging Port & Padded Straps

3. Timbuk2 Command Laptop Messenger Bag

Our third Timbuk2 model pick is this bag from the Command range. Available in 7 color combinations and 2 sizes, it’s quite versatile in design. From a student to a business worker, the simple and sleek construction can suit many styles. Dual aluminium buckles sit at the front and are backed with reflective hits to easily access them in the dark. The quick-access easy CAM buckle can be altered in seconds, requiring just one hand to lock and unlock. Plus, there is an adaptor strap for roller luggage.

3 Napoleon side pockets let you access the contents without even needing to lift the flap. They’re perfect for stashing sunglasses, power cables, your wallet and phone, and so on. One of these hidden pockets is even large enough for a standard U-lock, making it convenient for bike riders.

Self-sealing Velcro corners underneath the flap ensure an even tighter seal once everything is closed. The third waterproofing feature is the double Velcro panels that attach to the flap. As noted in the previous listed model from this brand, there are removable Velcro silencers. We love these because you can choose to stay quiet when in a business meeting or at the library.

Key Features:

Completely Waterproof TPU Lining & Outer Oxford Nylon Fabric
Extra Protection with Velcro Ears & Optional Velcro Flap Attachments
Various Secure Stash Options Perfect for Bike Riders

4. NEWHEY Waterproof Canvas Leather Messenger Bag

Our next choice is another old-school version with handsome waxed canvas and high-quality cowhide leather trimmings. For the buckles and clips, solid zinc-alloy metal is rust-resistant to ensure longevity. Strong load bearing is further enhanced with the tensile stitching.

Much like a vintage leather jacket, it stretches overtime to develop even more of a vintage look and feel – this is made to last. The sturdy construction makes it stand up on its own, so you don’t need to worry about it falling over and the contents breaking.

The front buckles are more of a fashion statement, as they close with a magnetic button. It makes it much easier to open and close, especially if you’re in a hurry. Underneath, you’ve got a full-length zipper, which keeps the contents safe and provides additional security.

You can fit a laptop up to 15.6” long, which is one of the most standard sizes on the market. To keep a snug fit, there is a padded sleeve that locks your laptop in with tough Velcro. A wide strap design for the main shoulder handle allows you to wear it over one shoulder, or across the body, both comfortably. A bonus top handle lets you grab-and-go in a hurry.

Arranging items cleanly is easy with various storage spots. A middle divider in the main compartment keeps books, papers, electronics, and other delicate items separated from everything else. A large zippered pocket lets you hide things, plus 2 inner open pouches for easy-to-reach things like pens, your phone, and keys.

Key Features:

Highly Dense Waterproof Waxed Canvas & Premium Cowhide Leather
7 Compartments for Easy Organization
Easily Removable Shoulder Strap

5. Peacechaos Waterproof Waxed Canvas Messenger Bag

Heading back to the old-school style, this consists of high-grade waxed canvas with genuine leather trimmings and bronze hardware. It’s extremely modest in design and sticks to the ageless outward buckles and durable leather shoulder strap padding. This is our favorite choice for carrying a 14” Macbook, as its dimensions are 15″L x 11″L x 4.7″L.

In terms of organization, it’s not the most innovative out there, but it clearly sticks to its theme of simplicity. In addition to the main compartment and laptop divider, there are 2 slip pockets, 1 zip pocket, 2 pen holders, and 2 front pouches. There is definitely plenty of space for textbooks, notebooks, papers, and so on.

Even though the canvas exterior is waterproof, a nylon lining amplifies the protection to make sure that the contents stay safe and dry when exposed to moisture. Considering the outer buckles only close with some magnets, the zipper is important for closing everything firmly.

We like that it’s much lighter than a full leather bag, so it won’t further weigh you down when you’ve packed any heavy items.

Key Features:

Gorgeous Waterproof Waxed Canvas & Vintage Leather Construction
Secondary Security with Full-Length Zipper Under Flap Closure
Secure Compression Padding Strap for Laptops

6. Shangri-La Waterproof Messenger Bag

For both men and women, this is a much smaller option that serves as an alternative to a regular large capacity messenger. It comes in small and medium sizes, both with a super retro appearance that will continue to age for that worn-in look. For reference, the small can fit an 11” iPad Pro, and the medium can fit a 12.9” iPad Pro.

The canvas feels stiffer in winter and softer in summer, so it adapts itself to the changing seasons. As well as being waterproof, the waxed canvas is fully rip-resistant for an increased lifespan.

Although there is the vintage front buckle, it uses a magnetic snapping system that makes it much easier to open and close. For added secureness, the inner zipper keeps everything shut. The zip, buckle, and other hardware are made from a gold-plated steel, adding class and durability. The shoulder strap is conformable, ranging between a 32” and 60” drop. You can customize the length at any time with a simple adjustment clasp.

Along with the spacious interior compartment, there are open holders to fit a phone or wallet, and another pouch. 2 external pockets, one on the front and one at the rear, provide additional space to keep valuables. There is enough room for the essentials plus a little bit more.

Key Features:

100% Cotton Waterproof Waxed Canvas & Genuine Leather Parts
Small: 11.3”H x 2.7” W x 9” L Medium: 13.5”H x 3.5” W x 9.7” L
Easy Magnetic Flap with Inner Zipper Closure

7. Kingsons Anti-Theft Waterproof Messenger Bag

This model from Kingsons is probably one of the most modern versions of the messenger that you can find out there. It rests much closer to the chest or upper back area, adding to the anti-theft notion. The main anti-theft theme comes from the highly secure main zipper design. It’s hidden away behind the front section of the bag.

What’s more, there are several hidden storage pouches, including one in the actual shoulder strap. This part has RFID blocking technology, so it’s the perfect place to stock your wallet or credit cards. Inside, there isn’t heaps of room when compared to a traditional model, but the ability to organize all your items is easy.

You’ve got a laptop compartment, smaller device pocket (both with a long, padded security strap), then various stash pockets and a bottle holder. On the side, you’ll find a USB charging port – simply connect your power bank and charge devices in a cinch.

With a full nylon body construction, you’re getting high performance waterproof abilities even in heavier downpours. Each zipper has a watertight seal, with the main one concealed by a cover. Since this has such a compact design, the multi-panel ventilation padding allows it to breathe when it’s against your body. The strap is very thick and breathable, made from robust polyester that is water repellent and tear resistant.

Key Features:

Fully Waterproof Nylon Fabric with Watertight Zippers
Hidden Back Safekeeping Pockets & Highly Organized Interior
Slim Sling Design for Heightened Security

8. Manificent Mens Messenger Bag

The last one on our list comes from Manificent. It has a timeless look but is packed with many convenient features to accommodate to the modern person. Another waterproof waxed canvas model, it’s highly durable, fully waterproof, and also scratch resistant. For the trimming parts, premium leather enhances the rugged look. The interior is pure cotton fabric, plus you have reinforced seams that greatly increase the strength to hold heavy items.

A large capacity consists of 16 different pocket and pouch storage possibilities. Inside, there is a padded laptop sleeve with a thick divider to further cushion a computer. There are several open pockets for your phone and pens, then a concealed zippered pouch. Outside is where the magic happens, with the hidden large pouch. It can fit so much stuff inside with heaps of compartments, plus there is a mesh pocket to keep electronics.

For comfort, the adjustable shoulder strap has leather padding to release shoulder pressure. You could even use it as a briefcase with the top leather handle. It can stand up on its own, so you can set it down anywhere without worrying about it falling over.

Key Features:

High-Quality Waterproof Waxed Canvas with Premium Leather Accessories
16 Customary Organization Compartments
Reinforced Stitching, Easy Buckle Snaps, Zipper Closure

9. Timbuk2 Commute Messenger Bag

A second choice from Timbuk2, this is a nylon version that still has the extremely classic design. It’s another huge best seller from this brand, plus you’ve got 3 slightly different constructions from the Commute line. These are definitely a modern version of the classic style, with the updated materials and nylon sheen.

On these models, the front flap buckles are exposed plus the trademark 3 panel design that increases volume. The compression straps that connect to the buckles have sewn-in reflective hits, which let you condense the contents with ease even in the dark.

On top of the main flap, there is a small zippered pocket that gives you quick access to smaller belongings. Inside, 3 drop pouches are the perfect size for things like sunglasses, your wallet, phone, as well as an integrated keychain so you’ll never lose your keys.

On the opposite side, a large zippered pocket stretches across the whole bag to hide plenty of items away. Industrial-grade Velcro provides another security option when closing the main fold. It has a Velcro silencer attached so you can decide when you want the extra security, or when you just need the buckles to keep things safe.

The great thing about 400D nylon is how flexible, durable, and obviously, waterproof, it is. It lets you fit so much inside, without creasing, wrinkling, or overstretching.

With the secondary protection from the interior TPU liner, you’re getting double the defense against leaks. Another point of waterproofing is the corner Velcro ears, that create a tight seal once closed.

Key Features:

High Performing 400D Nylon Fabric & 100% Waterproof TPU Lining
Tons of Interior & Exterior Storage Pockets
Highly Padded Crossbody Strap Plus Grab-And-Go Top Handle

10. Lymmax Waterproof Messenger Bag

This next one is our top pick for college students. It has a very simple outward design, with a choice of black or gray, and a modern feel to it from the sharp lines and flat rectangular shape. With the simple clip design, the padded straps can be adjusted to 3 different configurations. Wear it classically over the shoulder, swing it onto your back, or remove the straps completely and carry it by the smaller handle.

4 front open stash pouches sit below a very long zippered pocket, great for hiding any electronics and keeping them safe from scratches. The stash pouches consist of 2 larger and 2 smaller ones, which are the ideal size for pens, lip balm, and other little items.

A rear laptop section with a wide padded protective strap keeps your computer tucked in without room to move around. On the side, there is the convenient charging port, a highlight feature for students who always need power on the go. Exterior storage is also possible, with a hidden front pocket and a back open flap section.

There is no information on the outer material, but it certainly looks like nylon as it appears soft. For the inner textile, it looks like a ripstop nylon taffeta due to the high sheen. This will not only keep things dry, but is also resistant to tears.

Key Features:

Waterproof Nylon Fabric with Inner Lining
3 Carrying Options Over Shoulder, One-Handed, & Backpack Style
Lightweight 1.7 lbs Adds No Extra Weight with Huge 16L Capacity

How to Choose a Waterproof Messenger Bag

Materials

The most commonly used materials for this bag style are waxed canvas, and nylon. There are a couple of other fabrics that you can find in many current models, so let’s break everything down:

Waxed Canvas – this is typically used for vintage or traditional style messengers. It provides that worn-out rugged look that adds so much charm to an otherwise simple bag. Although canvas is inherently waterproof, the wax coating provides an additional layer of protection, from scratches as well as moisture.
Leather – leather is often used in conjunction with waxed canvas. You’ll usually find it on the trimmings of the bag, like on the buckle straps, and used as padding on handles. Though, it certainly isn’t uncommon to find full leather versions.
Nylon – for modern editions, this is the most used material. It’s super durable, waterproof, can be molded with many colors, and is flexible to allow plenty of wiggle room to pack items. Nylon taffeta is also often used as a lining for extra defence.
Oxford Nylon – this is a version of nylon that is also extremely durable. It’s smooth, has a slight sheen to it, and is popular with travellers because it’s easy to clean.

Top Tip: remember that leather and waxed canvas will often have a very weathered look. This is purposeful, as it complements the vintage aesthetic. It will continue to wear overtime, so if you don’t like this kind of look, stick to nylon or oxford nylon for a sleeker and more modern feel.

Capacity

What are you going to put inside your bag? Will you be regularly carrying your laptop? Books? Drink bottle? Other little loose ends? It’s important to look for a bag with the right amount of storage options so that you can get the most out of it. If you can’t fit your essential possessions, plus a little extra, then the bag has lost all its functionality.

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Take note of how the bag spits up its capacity. Are there divided compartments? Look for a combination of open stash pockets and zippered pockets, so that you have the choice to hide items or keep them at easy reach. Also, a padded laptop sleeve is something we recommend looking for, as it will ensure a snug fit, so your computer doesn’t slip around.

Strap

This is a huge deciding factor and shouldn’t go unnoticed when deciding on the right model. We suggest picking something with a padded sleeve. Either leather or some sort of foam is a huge advantage, as it relieves so much pressure on your shoulders.

To keep your phone safe and other valuables, try the smaller waterproof pouches

An adjustable strap is also crucial. It gives you the freedom to personalize the weight distribution, change up the style, and get the right level of comfort. Some brands have an easy one-handed clip system, like Timbuk2, but a simple buckle adjustment will work fine. It all depends on your personal preference.

Weight

These aren’t the most lightweight of bags when compared to other styles out there. This is because they need to carry a lot of stuff – you’ll probably be transporting your laptop, perhaps another device like an iPad, books, papers, umbrella, a drink bottle, wallet, keys, and everything else. Nylon will be a little lighter than waxed canvas and leather, but it all depends on the brand, construction, and materials. Even though one bag might look identical to another, manufacturers often have different design methods.

Style

One of our favorite things about messengers is that they are one of the most stylish options you can find. Particularly for men, it can be difficult to find a bag that will suit a certain style. Backpacks might not always complement your business attire, belt bags are way too small, and there aren’t many other choices out there for men anyway.

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Another style aspect is how you wear it. Every messenger is worn over the shoulder, but there are variations. Some are more slim-fit, like the one from Kingsons, and some can be converted into a backpack, like the Brass Tacks Leathercraft model.

Fastener

The closure method is also something to ponder over. Will you be constantly in and out of it all day? Do you want something more discreet, or you don’t mind what it looks like? Front buckles are the most common fastening method, but many brands have done an upgrade with magnetic clasps – it’s more user-friendly. An inner zip or Velcro attachment is great, as it adds another layer of protection.

Frequently Asked Questions

Are Messenger Bags Bad for Your Back?

While some may see the backpack as an “upgrade” from a messenger, this isn’t always the case. It truly all depends on how you are wearing each kind of bag. If you wear either one wrong or they are made from lower-end quality materials, this can lead to lower back or shoulder pain.

Backpacks should be worn on the upper back, sitting very close and snug to the skin. If they are worn loosely with the longest setting on the straps, it will put pressure on the shoulders and lower back area.

Messengers should also be worn quite snug to the body for the most comfort. Also, if the bag has the right padding on the strap or handle, it will release a lot of the weight and reduce pressure on the back and shoulders.

How do You Clean a Waterproof Messenger Bag?

For waxed canvas and leather bags:

Use a simple cold water and mild soap solution for the canvas and replace with warm water for the leather areas.
With the soft side of a sponge, massage the areas gently.
Use a separate clean, dry cloth or sponge and pat the wet areas.
Let it completely air dry.

For nylon bags:

Check all labels and with manufacturer to see if there is a recommended method.
Otherwise, turn the bag inside-out and shake any debris out.
Use a solution of warm water and a few drops of mild soap.
Dampen a cloth or sponge solution, gently wipe and use a soft-bristle brush for stubborn stains.

What Can I Put in a Messenger Bag? Is My Laptop Safe?

Anything you want! Well, anything that will fit. Use it just like a regular bag, but the great thing about this style is that they are the ideal shape and size for all kinds of laptops.

As long as there is a separate padded section dedicated to fit computers, your laptop will be secure and safe. A padded sleeve is also great for protection, as it keeps the laptop extra snug.

How to Waterproof a Messenger Bag?

It is certainly possibly to spray it with a waterproofing spray, which you can find at many retailers and online. However, we strongly recommend that you purchase outright an already waterproofed model. It will save you time and money in the long run, as you won’t need to continuously waterproof it, and they are already pre-sealed and graded by the manufacturers.

Conclusion on the Best Waterproof Messenger Bags

For bikers, businessmen and women, students, and everyone else, a waterproof messenger bag is one of the best portable storage solutions on the market. With such a distinguishable, yet unique, design, our list has covered all kinds of styles ranging from classic to contemporary.

As a slightly smaller alternative to some backpacks, they can still hold a lot of items, plus they’re the perfect size and shape for laptops (as long as you get the right size). The waterproof feature provides a highly convenient form of protection.

With adjustable shoulder straps, or the option to wear as a backpack for some models, these bags can sit flush to the body letting bikers ride around even in heavy rain. They are practical, keep belongings at easy reach, help you stay organized, and can complement any style.

10 Best Waterproof Messenger Bags in Canada for 2023

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