The Best Messenger and Crossbody Bags

The Mission Workshop Khyte is a modern take on the classic messenger bag. Built to be fully waterproof, the Khyte is designed for heavy use. The interior pockets are intuitive and expansive; every time I thought I couldn't fit more stuff into it, I found extra room and pockets. This bag is practically a hiking backpack. It can carry just about anything and stay bone dry at the same time. There's plenty of style to go with the substance too.

The exterior closures are magnetic and snap securely and easily into place, and it supports Mission Workshop's Arkiv system, so if you don't have enough pockets and pouches, you can always add more. The Khyte is not the kind of bag you throw a tablet into and carry to a café. It's the kind you bring when biking to work in a rainstorm.

Soft and lightweight, the Greenland Pocket is an excellent everyday bag. It's big enough to carry a Nintendo Switch, a notebook, and a variety of essentials. The cotton and polyester exterior is water-resistant enough to stand up to Portland rainfall, and it's really soft—so much so that I sometimes wonder if I carry it around just to pet it. It's also a stylish option that pairs just as well with winter wear as it does with lighter spring and summer outfits. Overall, this is one of my all-time favorite small-sized shoulder bags.

Filson is a Seattle-based maker of outdoor clothing and gear that's renowned for its durability—the company's roots are in outfitting miners for the Klondike Gold Rush.

This bag has a naturalistic look thanks to its camel color, but its made from rugged 500D water-resistant dry-waxed Cordura nylon canvas and has a thin layer of foam backing to protect your laptop or tablet and keep the bag's shape. Inside you'll find two zones divided by a thin foam-filled layer and two pockets perfect for holding a phone or paperback. In the front you have two zippered pockets with dividers. This is a bag that feels sturdy and, thanks to the waxed canvas, is water-resistant enough to not worry about even in heavy rain. I love the look of the hunter-orange front panel and the leather zipper pulls. —Martin Cizmar

Bellroy's Tokyo Work Bag is a deceptive little thing. From the outside it looks like any other messenger bag—if a bit more stylish. But once you open it up, that's when you start to realize this isn't any old bag. Inside you'll find a wealth of thoughtfully placed pockets and dividers that make it easy to keep your cables, batteries, and precious trinkets all safe and separate from each other. It seriously feels like it's bigger on the inside. It also has a padded pocket big enough to fit a 16-inch laptop.

Even when it's fully stuffed, it never balloons too far outside its ideal silhouette, which is always a plus. The exterior is made from recycled polyester, and it includes a luggage strap on the back so you can plop it over the handle of a rolling suitcase.

Waterproof and built to last a lifetime, Chrome’s Mini Metro messenger bag is a classic. From its signature seatbelt-buckle strap to its double-clasp closure mechanism, this is designed with the life of a bike messenger in mind. You load it up and swing it around your back, keeping all the essentials safely packed away.

The waterproof finish and liner are heavy-duty too. I carried one of these for years through storms and snow. Each time, it was fully loaded with a MacBook and an assortment of notebooks, and everything managed to stay dry. The Metro is also a great choice if you need a little more storage space, as it will carry everything you need to and from the office.

WaterField’s Shinjuku messenger bag was designed with the iPad in mind, and it shows. The interior pocket fits the iPad Pro 11 with a little room to spare, offers a spacious central pocket, and the lid flap seals with a magnetic closure. The thing that makes it a great bag for the iPad though is its size. It's not just small—there are lot of bags that are small and can fit an iPad—but this one gives your iPad room to breathe without feeling over- or under-sized.

Small bags can feel tight with an iPad stuffed in there along with other accessories like a power cord, Apple Pencil, phone, and other everyday carry items. Others can feel way too big, like your iPad is swimming around loose inside a massive bag that feels awkward to carry around with you everywhere.

The canvas option uses the X11 fabric from X-Pac, a high-tech canvas with interior structure and a PFAS-free durable water- resistant coating. It's durable, scuff resistant, and surprisingly water resistant. It held up to some heavy Seattle rain and kept everything inside nice and dry.

The Everyday Sling comes in a variety of sizes, but my favorite is the 10-liter version. It's technically a camera bag, but it also works as a standard small messenger. With ample pockets for organization and optional flexible dividers (to store a camera body and a lens), this bag can also comfortably fit a MacBook Air, a charger, and plenty of other accessories. Even fully loaded, the Everyday Sling maintains a slim profile that makes it easy to keep it close to your body. The strap is made from a seatbelt-like material, designed to slide easily over clothes, and it doesn’t bunch up on your shoulder as some straps do.

It's spacious enough to carry makeup, my 11-inch iPad Pro, a power bank, and loads of other random supplies. And it's comfortable to carry either slung at the side or cinched up like a backpack.

The Peak Design Field Pouch V2 excels in its role as a small everyday-carry bag for a couple of reasons. First of all, it's weatherproof and doesn't soak up water even when you're out in a rainstorm. Second, the horizontal orientation and slim profile make it a surprisingly spacious but ultra-low-profile bag to carry around. It's big enough for a smartphone, wallet, and small camera, plus it comes with Peak Design's signature seatbelt-fabric-style strap, making it easy to sling around your body.

I was a fan of Savage Industries' EDC One bag, but even I had to admit it was a little too big and bulky for me. Then the EDC Two came out. This is essentially a smaller version of the original, which makes it much comfier to wear for long periods (even when it's filled to the brim with farmer's market produce). The top opens up like an old-timey doctor's bag, revealing the entire interior, so you never have to dig around for things. 

The lining of the black version of the bag is a gorgeous high-vis orange that makes it easy to spot any small items that might otherwise get lost in the shuffle. Its generous size and tough, utilitarian design make it a great pick for makers, or for anyone who needs a hybrid toolbox and shoulder bag.

Made of simple, humble canvas, with just three pockets and a zippered pouch, this messenger bag is as straightforward as they come. It's inexpensive and lightweight, and it'll last you a really long time. I've had one since 2006, and while the color has faded a little, there are no holes or rips. Even with my stable of more expensive bags, I often pick this one up because it's not structured, and when carrying a light load it's pretty thin and light. It's not a good choice if you need something water-resistant though, as the canvas soaks up water like a sponge. 

Billingham bags have something of a reputation among photographers. These slick and stylish shoulder bags are renowned for their durability, understated style, and lifetime warranties. They aren't just for cameras though—they are excellent everyday totes if you're looking for a premium bag at a premium price. The Hadley 2020, in particular, is a perfect midsize bag that can fit a 15-inch laptop with ease, along with other essentials. It features two front pockets and a water-resistant exterior so it can withstand the elements. For more camera bags, read our guide.