No-BS Bag With a Bike Messenger Soul: Mission Workshop Monty Review

Plenty of messenger bags these days talk the talk. Most have a single shoulder strap, a classic profile, and, yes, generally hold stuff. But I’ve found that far fewer walk the walk (or ride the bike). There’s a reason they’re called messenger bags, you know.

If you’re like me, work remotely, and rely on two wheels to get around, you need something with a bit more street cred: Waterproofing is non-negotiable. The main shoulder strap needs a stabilizer to keep the bag centered while I’m riding, and the fabric has to be tough enough to endure kissing the pavement.

In my search, I’ve found that the Mission Workshop Monty pulls no punches when it comes to being the real deal. Crafted with precision and attention to detail, this bag embodies both style and functionality, which lands it atop my list of the best messenger bags out there — bar none.

To thoroughly test it, I performed capacity tests and packed the bag full of the items you might carry daily. I then did a comfort check, biking for miles and assessing its weight distribution and the strap’s comfort level. Read on to find out all the nitty-gritty details of this excellent bike commuter companion. 

In short: The Mission Workshop Monty ($220), with its rugged exterior, high-quality design, and thoughtful features make it an excellent choice for the bike commuter. However, it is decidedly more expensive than other messenger bags, and perhaps better suited to the more serious user. 

To see how the Monty compares to other high-caliber messenger bags on the market, check out GearJunkie’s Best Messenger Bags Buyer’s Guide.

Mission Workshop Monty: In the Saddle Review

First Impressions — The Full Monty

Right away, I could tell that the Monty was a high-quality bag. From the slick aluminum fasteners and waterproof zippers to the subtle branding, robust fabric, and large, smooth buckle, this is a design-forward messenger bag.

Its classic messenger silhouette is enhanced with modern accents, thoughtful organizational features, and waterproofed details. With multiple compartments, including a laptop sleeve and internal zippered pockets, it offers ample storage space for your daily necessities.

Available in a range of stylish color schemes and even the ability to choose the color of the buckle, you can customize the look to suit your style, whether you’re dressed for the boardroom or the coffee shop. The attention to detail, from the sleek metal hardware to the discreet branding, adds a touch of refinement to its rugged exterior. It is, in all, a good-looking bag.

While it is made to allow for a flap or roll-top closure, which is a nice feature, I wasn’t wild about the naked Velcro strips that are on the top of the bag when it isn’t in roll-top mode. But I was obsessed with the large, smooth buckle that allows you to adjust the strap easily. In one swift motion, you can loosen the bag, pull it around to your front, and grab anything you need without hassle.

On-Bike Comfort While Riding

When carried crossbody style, I found the Monty to sit comfortably high on your back. This allows it to stay out of the way while riding a bike and provides better weight distribution, especially if you cinch the strap snugly.

A detachable cross-chest stabilizer provides an even more secure fit, enabling the bag to stay in place. Additionally, the shoulder strap can be moved to either of your shoulders for right or left-handed access. 

The extra-wide, padded strap is one of the most comfortable I’ve tested. Its width allows for superior weight distribution, and its light padding protects you from any rubbing. A messenger bag will never distribute load quite as well as a two-strap backpack, which is why comfort is an extremely important metric. The Monty’s strap design makes sure your commute is as enjoyable as possible.

Organization for Your Essentials

Some people prefer a bag with a cavernous interior to dump their things in. Others prefer endless pockets so that everything has its place. Throughout my testing, I found the Monty to provide a happy medium between the two types: an ample main compartment and some thoughtfully sized smaller pockets for everyday accessories. 

I was seriously impressed with the capacity of this bag; a whole 21 L of volume provides ample room for a 15-inch laptop with plenty of space left over for books and accessories. The front has one medium-sized zippered pocket that can store a 13-inch laptop, which also has some smaller zippered pockets for other small or flat items. Lastly, there are two large pouches on the front of the bag protected by a Velcro flap for quick access. 

I’m partial to bags with organization like the Monty, because it can be overwhelming when there are so many small pockets and pouches that demand to be filled. The front pouches on this bag are easy to access quickly, though I wish they were big enough for a bike U-lock, which ends up needing to be stored in the main compartment.

Electronics Protection and Weatherproofing

Mission Workshop advertises this bag as being “weatherproof,” and it features some great design characteristics to protect your valuables from the elements. Its ripstop nylon liner is made with a fully waterproof TPU backing, its zippered front pocket is also waterproof, and when the front flap is folded down, the interior stays sealed shut from rain. Through all my testing, I found no moisture leaked in.

The biggest downside of this bag is its lack of a padded laptop compartment. If you have a larger laptop, you’ll have to put it in the main compartment with everything else, preferably in a protective sleeve. A smaller model will fit it in the front pocket, but it doesn’t provide any additional padding. For a bag of this price, I’d hope to have some extra protection for laptops, seeing as most of us frequently travel with one.

A Tough Skin With One Cosmetic Issue

The quality of this bag is high, evidenced by the burly 1,000-denier CORDURA shell and ripstop nylon/TPU on the interior. The top can be used in a traditional flap-down fashion, or affixed with Velcro for the rolled-up top configuration. This allows you to fill the bag to the brim and have quicker access to the front pockets. 

As previously mentioned, I don’t love the look of the naked Velcro when the flap is down, but you can easily wear it most of the time in the roll-top configuration if you prefer that look, and only put the flap down when you need the added rain protection.

Mission Workshop Monty Messenger Bag: The Real Deal

Overall, the Mission Workshop Monty Messenger Bag is a premium pack that combines durability, functionality, and style with ease. If you’re a frequent bike commuter, it’s important to have a bag that is comfortable to ride with as well as offers weatherproofing for the inevitable surprise storm. The Monty does just that.

While the high price tag and lack of a padded laptop compartment might be enough to put you off, they certainly haven’t ruined the Monty for me. If anything, it feels like investing in a pack that’ll really live up to the promises it makes, and that’s worth spending on.

If the 21 L of space in the Monty is just a bit too big for your needs, the Timbuk2 Classic is a slightly slimmer 16 Ls, and while it’s not quite as well balanced as the Mission Workshop bag, it too stays true to its roots. I don’t find it tough to fill those 21 L, however, and am sticking with the Monty for my rides.