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Our pick for a sleek and stylish commute, the Rains Commuter Bag, recently underwent a redesign. We’re in the process of testing the new version, the Rains Messenger Bag. Rigid Suction Nozzle
A good messenger bag will see you through almost any casual situation. Messenger bags are small enough that they won’t hit your fellow commuters on the train, formal enough to look at home in an office (without being as staid as a briefcase), and sporty enough to stay in place as you bike to a coffee shop to do some work. Two Wirecutter writers tested 18 messenger bags for two months, commuting with them daily. And since no two people or commutes are the same, we found the eight best options for anyone.
The Timbuk2 Classic Messenger Bag is reasonably priced, and it’s packed with pockets.
Get this if: You need an inexpensive messenger bag that has a classic look and a variety of useful features for organizing everything you carry.
Maximum laptop size: 15 inches (medium)
Why it’s great: The Timbuk2 Classic Messenger Bag offers a winning combination of well-thought-out features for the frequent commuter and a ridiculous number of organizational pockets, all at a reasonable price and with a lifetime warranty. This bag comes in multiple sizes (we tested the medium) and a myriad of color options, so the Classic Messenger feels personal and adaptable to any lifestyle.
The Timbuk2 is classic like a simple white T-shirt is classic—everyone looks good wearing one, and it never detracts from what you’re trying to do. It’s exactly the bag you picture when someone says “messenger bag.” Plus, thanks to the Timbuk2’s soft, airmesh shoulder strap, it was comfortable to wear even after an hour-long commute with it slung over a shoulder.
What helped the Timbuk2 stand out from other messenger bags was its variety of well-thought-out features for keeping the bag’s contents safe and organized. The Timbuk2’s interior has a waterproof lining to help protect your laptop and notebook from a sudden downpour, and the upper corners of the opening fold inward to reduce the chance of water leaking in when the bag is shut. (Waterproofing is fairly common in messenger bags, thanks to their bike-courier origins, but it’s not universal, and so it’s good to see this in an affordable bag.)
There’s a zippered cargo pocket (it reveals itself after you unbuckle the two front straps) that has a convenient keychain hook. If you don’t want to be constantly opening the entire bag, there’s also a hidden zippered side pocket, which you can stuff simple items into for retrieval with one hand.
There are two additional interior pockets that are tucked away, and they don’t add extra bulk if you don’t use them, so the bag doesn’t become bulbous. There’s a large padded laptop sleeve and plenty of space in the main compartment to stuff a hoodie or a sweater.
We also like the small nylon handle on the back of the bag, which made it easy to pick up the bag and move it around without having to tuck it under our arm like we were playing a game of rugby.
The Timbuk2 has a lifetime warranty—but it doesn’t cover wear and tear. And you will need to arrange and pay for shipping the bag to the company’s repair facility; the cost will vary, depending on where you’re shipping from and what service you use.
Flaws but not dealbreakers: Our biggest gripe with the Timbuk2 Classic was the overabundance of dangling straps. They made Jordan feel like a paragliding pilot. Although all the straps have a purpose, they kept getting in the way, which was frustrating considering this is a bag that’s built to be simple and functional.
Dimensions: 12.2 by 14.6 by 7.09 inches (medium) Materials: nylon Crossbody strap length: 50 inches Weight: 1.72 pounds Warranty: lifetime Colors: Monsoon, Black, Gunmetal, Lightbeam, Army Pop, Army, Bookish, Nautical, Rind Pop, Collegiate Red
The Vitesse Cycling Musette is a comfortable bag that makes up for its lack of features with a simple, straightforward design and a vintage aesthetic.
Get this if: You want a simple, compact messenger bag and are willing to sacrifice some weather resistance for classic styling.
Why it’s great: The Waterfield Vitesse Cycling Musette is unfussy and not trying to do anything other than be a perfectly simple little bag. If you need something that doesn’t take up too much space, and you lug around only a laptop and a few small accessories, the Cycling Musette is a good match for you.
This bag is comfortable, durable, and stylish. Its thick canvas construction and leather straps will make you want to wear a newsboy cap and hop on a penny-farthing. In 2021, it launched in a leather alternative. Although hyper-organized types might decry its lack of internal pockets and dividers, it still managed to win us over because of its simplicity.
The Cycling Musette’s comfort is due to its flexible but hard-wearing materials—its lack of internal structure and the canvas exterior mean that it shapes around your body easily and comfortably. The waxed canvas material looked appealing in the blue colorway—and it felt like it could take a beating. We also appreciated this bag’s 60-inch strap length (one of the longest we found), which you can adjust to suit your height or weight.
There are two small pockets inside this bag, so you can throw in your keys, a book, earbuds, or a notebook. The Cycling Musette also has a leather tab closure, so it stayed secure when it was stuffed with a hoodie, a 13-inch Macbook Pro, a few books, a glasses case, and a laptop charger. It’s also easy to open and close.
However, the Cycling Musette isn’t as tightly sealed or as rainproof as the Timbuk2 Classic messenger, and it might have some issues if you’re in a torrential downpour; even though waxed canvas can repel some water, it’s not as resistant as treated nylon. The bag is small and constructed of flexible material, making it well suited to transferring between trains during rush hour without knocking into anyone—unlike the much clunkier Waterfield Rough Rider.
The Cycling Musette also has a lifetime warranty, and people have good things to say about the company’s customer service and bag quality.
Flaws but not dealbreakers: The Waterfield Vitesse Cycling Musette lacks a built-in laptop pocket, which almost all of the other messenger bags we tested have. Without that extra padding or the sleeve for a designated laptop or tablet, the Cycling Musette doesn’t provide much protection for anything delicate you might be carrying. We recommend pairing this bag with a dedicated laptop sleeve, because the waxed canvas won’t protect items if you drop this bag or knock it into a doorway. Plus, if you overload it, you might end up feeling that water bottle digging into your back for your entire commute.
Dimensions: 10½ by 16 by 2¾ inches Materials: waxed canvas Crossbody strap length: 60 inches Weight: 1.9 pounds Warranty: lifetime Colors: Navy, Brown
Sleek, stylish, and restrained, the Rains is a little black dress of a bag, with a shoulder strap that’s more adjustable than most.
May be out of stock
Get this if: You want a refined, waterproof messenger bag.
Why it’s great: Since we tested, Rains slightly redesigned this bag and renamed it the Messenger Bag. We’re told that the fabric and the carabiner closure have been updated. And, unlike on the previous model, the straps are not padded—a feature we loved in the original design. We’ll test the new version as soon as possible.
The original Rains Commuter Bag (which is no longer available) we tested is the jack-of-all-trades option, with a little something for everyone. It has features similar to those of many great bags—like weatherproof materials and long adjustable straps—but the Rains bag really stands out for how well it all comes together. Its thin profile and good weight distribution kept the bag tight against us, so we could nimbly weave through commuting crowds and feel stylish while doing it.
One of the most notable features we discovered during our testing was how comfortable the Commuter Bag was. It’s unique in that there are length adjusters on either side of the shoulder strap’s central buckle, and they enabled us to adjust the bag more precisely, shifting the weight to what felt the best for each person. And the strap is padded on both ends. Thanks to all of these things, the Commuter Bag remained comfortable on the shoulders, regardless of who was wearing it.
This bag’s minimalist look allows it to fit a wide range of occasions, whether you need it to be a chic accessory or an essential tech carrier. Its style is deceiving at first. Though the Commuter Bag appears to offer little organization and no laptop sleeve, the laptop sleeve is actually hidden in the back of the bag, with separate access from the exterior, allowing you to grab your laptop without having to open the main flap and subject the interior to the elements. The inside of the bag may be too open-concept for many, but we imagine a true minimalist won’t have much to carry anyway. Haley—one of the writers and testers for this guide—is no minimalist, and she liked dumping everything in and masking the chaos in such a beautiful way. Compared with the Waterfield Vitesse Cycling Musette, which similarly offers very little organization, the Rains has a much sleeker style, as well as a few other niceties, like the more-adjustable straps and laptop sleeve.
The polyurethane and polyester material is waterproof, and the exterior access laptop pocket is protected by a flap of the same material, so water doesn’t drip in. And, based on our experience with other Rains bags made of the same material, we’re confident your electronics will be safe in the Commuter Bag. Plus, the thick, almost rubber-like materials add structure to the bag, giving your stuff a little extra protection from the elements. The Rains Commuter also has a two-year warranty, and though that’s not as good as the lifetime warranty of some bags we looked at, it’s better than those with a one-year warranty.
When testing, Haley’s sister observed that the black-on-black accents made this bag acceptable to wear with an Air Force uniform (PDF)—something many bags are not. Although you should always consult the particular regulations of your own armed forces branch before purchasing a bag, it’s nice to find a stylish and well-made one that may fit the bill.
Flaws but not dealbreakers: There aren’t many pockets on the Rains Commuter Bag, so there’s not much room for organization. If you’re someone who needs a little bit more organization, this bag may not be the one for you.
Dimensions: 11.8 by 16 by 4.7 inches Materials: 50 percent polyurethane, 50 percent polyester Crossbody strap length: 45½ inches Weight: 1.77 pounds Warranty: two years Colors: Black, Charcoal
With its more-structured build, the Martel bag resembles the classic camera bags of yore, while also offering a simpler, modern look and the laptop compartment you need.
Get this if: You want a structured bag and appreciate a vintage-influenced aesthetic.
Why it’s great: The Matt & Nat Martel Messenger is at the crossroads of professional and pretty. With its structured design and canvas construction with vegan-leather accents, it has a classic look that reminded us of a vintage camera bag.
The straps are 50 inches at full length, which is pretty average for most bags. Even though they were perfectly long enough for Haley (who is 5 feet 7 inches), Wirecutter staffers who were taller or who had broader chests or breasts noted that it was a little more difficult to find a comfortable length for them. (Of our cross-body picks, the Waterfield Vitesse Cycling Musette, the Waterfield Executive Leather Messenger, and the Knomo Kinsale are the only ones that have longer straps.) If you take off the removable straps, you can wield the Martel like a briefcase: This isn’t a common option, so it sets the Martel apart from most other bags we tested.
Its spacious interior has room for small lunch boxes, makeup bags, books, and just about anything else you could think of bringing with you on a daily basis. Though the inside doesn’t allow for much organization, it does feature a padded laptop sleeve, fitting a laptop up to 13 inches. The combination of structure and padded sleeve should leave you feeling secure that your laptop is in good hands … or pockets. The front also has both a Velcro and a snap closure, keeping everything you want inside and everything you don’t want outside.
The bag’s canvas exterior is weather-resistant and durable, due to the tight canvas weave. But the Martel Messenger isn’t as waterproof as some other bags we tested, like the Chrome, Mission Workshop’s The Monty, or the Rains. You can treat the canvas with wax to make it more waterproof, but that changes the look and feel of the material.
Flaws but not dealbreakers: Haley found the structured build to be a little irritating against her petite (120 pounds) frame. It knocked on her hip during her commute, partly due to the lengthy straps and partly due to the structure, so it proved to be a little clumsier to maneuver on a crowded subway. However, the structure made her feel like her personal items were well protected.
Matt & Nat offers only a one-year warranty, which is on the low end for a messenger bag, especially compared with some other options that have lifetime backings, like the Timbuk2.
The canvas material is also susceptible to scratching. Haley found that it appeared more worn or dirty than she would have liked, but she also acknowledges that she’s a little more chaotic with her things. Plus, who doesn’t like a little wabi-sabi, the Japanese theory of accepting and embracing imperfection.
Dimensions: 15 inches by 12 inches by 5½ inches Materials: canvas, vegan leather, nylon Crossbody strap length: 50 inches Weight: 1.55 lbs Warranty: 1 year Colors: Black, Olive, Chili Matte, Nickel
With its strong seat-belt strap, weatherproof materials, and large laptop pocket, the Chrome Citizen bag will keep your personal items safe on your commute.
Get this if: You commute by bike and are looking for extra security.
Why it’s great: This bag is a cult classic among bike riders and messenger-bag enthusiasts alike. To the uninitiated, the design seems a little cumbersome—the bag is big, bulky, and pretty utilitarian-looking. However, the Chrome Citizen Messenger Bag lived up to its reputation, standing out from the rest because of its great weight distribution, comfortable shoulder strap, and organizational features. It may be safe to say we’ve drunk the Chrome Kool-Aid.
The shoulder strap is known for its distinctive seat-belt buckle, which secures the strap to your person, much as an actual seat belt would. Thankfully, it’s padded, to prevent the strap from digging into your shoulder over the course of a long commute. The Citizen also has a stabilizing strap—a smaller tie that runs from the main one to the corner of the bag—which keeps the bag solidly in place and secured to your body. If you’ve ever been biking with a messenger bag on your back and struggled with it slipping forward, this strap will prevent that. It also aids in the weight distribution of this bag.
The Chrome Citizen has plenty of organizational features, including a laptop sleeve, little pockets, and pen holders. The floating tarp liner on the inside also allows you to further separate items in your bag, so you can stash a wet rain jacket in your bag without it soaking through to your laptop. You can also customize your bag with inserts like the messenger organizer or the phone pouch. All of the bag’s pockets are protected by one large flap that both Velcroes and buckles shut. The Velcro was a little too much for Haley when she commuted by subway, since it was difficult to unstick and was pretty loud once it did. But that reassured us that personal items would be safe when someone was biking vigorously on rough roads.
Chrome has a reputation for long-lived bags, and the Chrome Citizen has a lifetime warranty. Like most lifetime warranties, it will cover only defects, not wear and tear, and the company gets fairly granular in what it will accept on the warranty page (notably, Velcro closures are covered for only two years).
Flaws but not dealbreakers: Although the seat-belt buckle is a favorite among many, one Wirecutter staffer wasn’t particularly sold on it. When testing the bag in our office, biker extraordinaire and appliance expert Tim Heffernan noted that someone could potentially apply enough pressure to dislodge the buckle, sending their belongings straight to the ground. Luckily, the stabilizing strap would act as a backup if that happened
Dimensions: 13 by 22 by 7 inches Materials: tarp and nylon Crossbody strap length: 35½ inches Weight: 2.8 pounds Warranty: lifetime Colors: variations of Black, Gray, Camouflage, Tan
The Monty Bag has a more streamlined shape than similar bags made by Chrome, and its minimal design is perfect for the biker who wants a less-intense messenger bag.
Get this if: You’re looking for a sturdy and flexible bike messenger bag, with the ability to either have a roll-top or traditional flap closure.
Maximum laptop size: 13 inches to 15 inches
Why it’s great: Mission Workshop’s The Monty stood out among the bike messenger bags we tested because it brings a sleek design to sturdy, utilitarian construction, plus its thick shoulder padding makes it more comfortable for long trips. After an hourlong commute, Jordan said the Monty bag’s pad made him feel like someone had attached a cloud to his shoulder. The pad is quite large and can be a bit awkward for the first few wears, but we soon realized it’s one of the bag’s best features. If you’re riding with this bag on your back for a long time, you want those pads to feel secure and, most importantly, comfortable.
Like the Chrome Citizen, the Monty bag has a stabilizing strap to keep the bag cinched high and tight against your back when you’re biking or on the move. This secondary strap is often the hallmark of bags designed specifically for cyclists.
Unlike some other bags we tested, like the Brooks Brother Canvas Messenger bag, the Monty bag retained a clean shape despite the fact that we packed it up like a burrito. The Monty is the only bag that gives you the option of closing it as a roll-top or with a traditional flap, depending on how much space you need. We appreciated being able to adjust the bag depending on the situation, and this made the Monty bag seem much more adaptable.
The Monty is waterproof, and, like the Chrome, the interior is made of a sleek, water-resistant material, so it’s easy to wipe up any liquids that may end up inside the bag. (If you’re anything like Haley, this feature will save your hide, and maybe even your laptop.) There’s an internal zippered pocket that can fit a 13-inch laptop, or a small tablet and a book. You can also use the main compartment, which is meant to house a 15-inch laptop. For headphones, a notebook, or other small knickknacks, the Monty bag also has two small cargo pocket sections.
Mission Workshop’s The Monty comes with a lifetime warranty—which, as with most bags, doesn’t cover wear and tear. But we’ve heard that the company has excellent customer service.
Flaws but not dealbreakers: You’ll have to be mindful of the loudest Velcro sounds ever created when you open this bag. It sounds like someone decided to do construction right outside your home at 6 in the morning. Despite the noisy closure, Mission Workshop’s The Monty inevitably makes up for that small issue with its comfortable padding, roomy main compartments, and versatile closure options.
Dimensions: 10 by 16 by 5 inches Materials: nylon Crossbody strap length: 40 inches Weight: 2¾ pounds Warranty: lifetime Colors: Gray, Navy, Black, Olive, Red
This is the best, most affordable leather bag we tested, with its full-grain leather, organized interior, and lengthy straps.
Get this if: You want a stylish and well-organized bag constructed of full-grain leather.
Why it’s great: The Knomo Kinsale is an elegant leather option for half the price of many other similarly constructed bags. The full-grain leather, uniform design, and slim profile make it more adaptable to traditional business environments while still feeling modern. Despite its trimmer build, the Kinsale also features a snug laptop pocket, organizational compartments, and overall good structure.
The Kinsale’s strap length comes in at 59 inches, allowing you to more easily find a length that suits you. The strap lacks the bulk of a shoulder pad, so it’s not ideal for really heavy loads. But the straps are wider and flatter than most, so the bag is comfortable on an average commute with a few items stashed inside.
The Kinsale’s size and shape also allowed us to more easily navigate tight spaces, such as packed subway trains. Our belongings felt well protected by the thick, structured leather exterior and amply padded pockets. Canvas bags, like the Waterfield Vitesse Cycling Musette, always feel a little riskier for laptops and electronics, but a solid leather bag like the Kinsale feels more trustworthy. To keep your life organized, the bag has a 13-inch laptop sleeve, as well as smaller pockets for various personal items.
The Kinsale has a magnetic closure on the inside of the flap that allows you to quickly access the bag’s contents during a commute. Thankfully, the flap is also long enough that it fully covers the entire bag, so the inside is less exposed than you might think—a pickpocket would have to lift the whole flap to get in. However, that does mean that if the bag falls over, or if you have a more-active commute, like a lengthy bike ride, the magnet might pop open.
Flaws but not dealbreakers: During our panel test with fellow Wirecutter staffers, some noted that they didn’t like the brighter-colored interior of the Kinsale. Some found the yellow accent on the inside of the black Kinsale to be gauche, but others liked the stark contrast. The lighter interior does enable you to find stuff inside more easily, but it will also show dirt.
Our Wirecutter testers also noted that the straps’ base is located on the back of the bag, which causes the Kinsale to tilt forward slightly when it’s resting on your body. This doesn’t hinder the use of the bag, but some found it to be a little awkward.
The Kinsale is backed by a two-year warranty, which is on the low end for a messenger bag. Knomo also recommends treating its bags with a leather conditioner multiple times a year, to maintain the leather’s feel and suppleness.
Dimensions: 9.9 by 13.8 by 2.9 inches Materials: leather Crossbody strap length: 59 inches Weight: 2.8 pounds Warranty: one year Colors: Black, Brown
The Executive Leather Messenger bag has a hefty price tag, but it’s worth it if you are looking for a well-constructed and meticulously designed messenger bag to keep for the long haul.
Get this if: You’re searching for a leather messenger that you can keep for years to come, and you need something that fits in with stylish or professional environments. Maximum laptop size: 16 inches
Why it’s great: The Waterfield Executive Leather Messenger is a beautifully designed bag, allowing everything you place inside to line up perfectly symmetrically—like a scene from a Wes Anderson film. Its leather is thicker and more protective than that of the Knomo Kinsale, with more internal pockets, plus a clasp rather than a magnetic closure. It also has a far more generous warranty.
But what struck us most was how everything seemed to fit just so. When you use the Waterfield Executive bag, everything is perfectly laid out, and if you place your items in the right spot, you won’t have to search aimlessly for paper or a pen—all of your items fall into place, like in a game of Tetris. Your keys just happen to hang on the metal key fob off to the side, your pen can fit perfectly into one of two designated slots, and your tablet has its own mini padded compartment. And if you carry around a small notebook, the bag has a secure place for that as well. (Some other bags have a habit of devouring small items and turning into a black hole whenever you need to find something in a pinch.)
The bag’s interior is a smooth, gold-colored liner, which makes your gear easier to find—and also makes it feel a little like it’s being hugged by Big Bird. The laptop sleeve should fit computers that are between 13 inches and 16 inches. Its padding means you shouldn’t have to worry about your laptop getting scratches or dents. There were a few times when we bumped into a wall with the bag, but after we checked our laptops, there wasn’t any sign of cosmetic damage.
The Executive Leather bag is made of a smooth, thick, full-grain leather that felt more resilient than that of the Knomo Kinsale. The leather flap and buckle make it easy to retrieve items on the go with one hand, plus it felt more secure than the magnetic closure on the Knomo Kinsale. The adjustable shoulder strap reaches up to 64 inches in length, the longest of any bag we tested, so it’s well suited to people with longer or thicker torsos. And in our testing, we found it can shorten considerably if you wear the bag high or are on the shorter side. The Waterfield Executive also comes in two sizes: full and compact. We tested the compact size, and think the full-size option is better suited to a person who needs to carry a larger laptop, like a 16-inch Macbook Pro. Waterfield also offers a lifetime warranty, which helps justify the price premium over the Knomo.
Flaws but not dealbreakers: Compared with some of our other messenger bags, the Waterfield Executive Leather can feel like the weight of the world is hanging off your shoulders. It can often be uncomfortable to carry for long periods of time. Jordan also found its shape to be quite obtrusive in certain situations during his commute: He said it felt like a large Lego brick was attached to his back. Numerous times during a commute, he accidentally bumped into a person and was given the New York stink eye. The size issues are a tradeoff for the bag’s ample padding and many pockets (both of which we really like). We also found that some of the other color options looked radically different compared with the black leather; they looked more rugged and less appealing, but functionally the bag itself was the same.
Dimensions: 10½ by 14¼ by 2¾ inches Materials: full-grain leather Crossbody strap length: 64 inches Weight: 3¼ pounds Warranty: lifetime Colors: Chocolate, Black, Grizzly
If you’ve ever received a death glare for carrying an overstuffed backpack on a crowded commuter bus, then you understand the need for a messenger bag, which lets you swing the bag out of the way quickly and easily. If you’ve ever been biking and needed to pull something out of your bag without having to take it off completely, then a messenger bag is for you. For those who think a backpack makes them look like a child and a briefcase makes them look like a corporate stooge (we tend to disagree on both counts), a messenger bag could be just the thing.
Whether you’re trekking into the office or lugging your books halfway across a college campus on a bike, a messenger bag will suit most working professionals and students—they’re flexible bags that can look equally good holding just a book or loaded up with a full day’s worth of gear. Compared with a briefcase, a messenger bag is easier to carry since it’s designed to be worn over your shoulder rather than carried by hand. And it won’t end up looking overstuffed just because you decided to throw a sweater inside. Laptop totes aren’t as easy to swing around to your back if you’re biking, and they tend not to have closure systems that are as good as those on a messenger bag. Backpacks are more ergonomic than either of those, because they split the load over both shoulders. But they’re harder to move around in tight places, and you have to take them off entirely to get things out.
One caveat about the messenger bag: Shoulder bags can be bad for your back. “The worst culprit for back pain is the shoulder bag because it causes the spine to bend in one direction and the shoulder to fall forwards on the carrying side,” physiologist Lucy MacDonald told Women’s Health magazine. “This puts excess stretching and compression forces through the different structures, which causes injury,” she said. This doesn’t mean you should stop using messenger bags, but in our research, we looked for bags that emphasized comfort and kept ergonomics front and center.
Sometimes our guides are best written by enthusiasts, and other times skeptics uncover more useful perspectives on a product. It’s safe to say that when we first began writing this guide, neither of us—Jordan Bowman and Haley Sprankle—were on the messenger-bag bandwagon. We were both pretty set on backpacks for our day-to-day commutes, switching it up occasionally—Haley with her Kate Spade tote bag, when she was feeling fancy, and Jordan with his media totes on a weekend stroll. But over the course of writing this piece, we came around to the idea of messenger bags being a useful way to carry your gear to work.
We asked staffers around our office about what they looked for in messenger bags. Many noted how important it was to keep their personal items secure, others said that organization was key, and some said that looks were just as important as anything else.
With this in mind (combined with what we knew about how uncomfortable it can be to carry a bag on your shoulder all day), we searched for (but didn’t solely limit ourselves to) bags that:
While chatting with others, we also came to realize that not everyone’s messenger bag needs are the same. Some people have intense commutes, biking several miles to work a day; others brave the subway on their way to work; and many get in their cars and sit in traffic. Based on that array of needs, we decided to order the bags by:
This left us with 18 bags to test, each fitting into one of the specific categories above and having some combination of the desired features. We took these 18 bags out into the real world to see how they worked. We stocked each bag with our regular goods, always including a laptop, a laptop charger, a notebook, a book, a phone, pens, and a clothing item. Jordan traditionally kept his bags more orderly, and Haley chaotically threw her life into hers. We traveled both long and short distances with each one, literally taking trains, planes, and automobiles. We consulted our more-serious in-office bikers, as well as a 10-person panel of staffers. In the end, we decided on eight bags, with two in each category.
The Bellroy System Work Bag was an overall great bag, but it ended up being too big for a daily commute. With its roll-top closure, featuring a magnetic G-hook, it felt like everything was safe and sound in the bag. This bag also offered plenty of internal organizational features, including a 15-inch laptop sleeve. But the luggage pass-through on the back really says it all—this bag is much better suited to a weekend work trip than to a daily commute.
The Côte & Ciel Riss Obsidian Black bag drew our eye immediately, but it ultimately left us uninspired. This unique, hexagonal bag had a similar sheen to the Rains Commuter Bag, but it lacked the Rains’s functionality. The mesh part in the middle of the bag seemed to serve little purpose and only altered the overall silhouette of it. The bag just felt too complicated for how minimal it initially seemed.
The Peak Design Everyday Messenger was very structured, and it is even advertised as a camera bag. Although its straps were easily adjustable and the interior organization was customizable, the bag just fell flat for us in the end. When we compared it with the similar Matt & Nat Martel Messenger, we thought the Everyday Messenger could use a little more style. If you’re looking for a good camera bag, or you like the look of this one, we still think it’s a good choice.
With its weather-proofing and reflective material, the BaileyWorks Super Pro seemed like it could be a good option for bikers, but in the end it was too flimsy to really even be in the running. The bag couldn’t retain any shape, and we never felt like our personal items were safe when we were wearing it. Plus, there were no real organizational features, leaving this bag on the outs with us.
The discontinued Brooks Brothers Canvas Messenger felt like Frankenstein’s monster: It was tailor-made for us, but it kept hurting us unintentionally. The gorgeous, classic design wasn’t enough to save this bag from all its flaws. It doesn’t hold shape very well, falling into a more frumpy, lumpy look when packed with any assortment of belongings. It also hurt our shoulders more than any other bag we tested. The thin, clipped-on straps provided very little support, making our day-to-day commutes unnecessarily painful.
The Waterfield Rough Rider Messenger—now discontinued—is massive, weighs about 3½ pounds, and, after an hourlong commute, it felt like we were carrying a kettlebell on our shoulders. And even if you disregard the weight, you’ll have to be cautious of this bag’s blocky shape. One of its best features is its rugged feel, and it seems like it would be able to withstand a significant amount of wear and tear.
This article was edited by Catherine Kast and Jennifer Hunter.
Jordan Bowman is a photography, music, and fashion enthusiast who has a tendency to make hip-hop references.
Haley Sprankle was an updates writer at Wirecutter covering kitchen gadgets and financial content. She loves French bulldogs, French tucks, and french fries. It’s a wonder she hasn’t been to France yet, but it’s next on her to-do list.
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