I’ve gone through my fair share of messenger bags, even before writing about them was part of my job. But Waterfield Designs’ Executive Messenger is hands-down the best messenger bag I’ve ever laid my hands on. 

Messenger bags are often very bulky, even when they’re not full. The leather Executive Messenger addresses this problem by being very slim, but flexible. There’s just enough internal structure to keep my gadgets safe but enough flexibility that after a few uses it will start to contour to your body a bit. Plus, it has ample interior pockets and pouches to store small things, like lip balm and charging cables. The interior lining is a bright orange, which helps with visibility. 

It’s a very stylish bag (very dark academia and scholar-chic), and it’s built to last, with a leather outer that has so far weathered nicely. They’re handmade to order, and that attention to detail really shines through. It feels sturdy, the seams are thick and robust, and the pockets and front latch seem like they’re made to last a lifetime. 

Waterproof and Also 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 a true messenger bag 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.

The Everyday Sling comes in a variety of sizes, but my favorite is the 10-liter version. With ample pockets for organization and optional flexible dividers, this bag fits a 13-inch MacBook Pro, 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.

This was my everyday bag for CES 2020, and it was a lifesaver. 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 carried either slung at the side or cinched up like a backpack.

Carhartt has a reputation for hard-wearing clothes and accessories, and the Crossbody Snap is no exception. The water-resistant polyester material is thick and sturdy, and the seams and pockets feel like they'll stand up to just about anything you throw at 'em. I'm always on the lookout for a small bag that can carry an iPad and a couple other accessories, and lately the one I've been reaching for has been the Crossbody Snap. It's just tall enough to fit an 11-inch iPad Pro, but it more comfortably fits the new iPad Mini. Plus, it looks nice with just about any outfit.

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 everyday essentials. The cotton and polyester exterior is water-resistant enough to stand up to heavy 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.

The Pearl crossbody is a lovely, elegant shoulder bag with two zippered pockets, a central compartment, and tons of internal organization. It's honestly the one I grab on my way out the door on most days. It's small enough that it's not bulky, and it's big enough to fit an 11-inch iPad Pro in the central pocket. Plus, it looks nice. It pairs well with most business casual or casual-casual outfits without being ostentatious.

I also like the fact that the pockets are accessible from the top, and not obstructed by a flap. That way I really can just reach down and grab my lip balms, or pick up a cool rock to put in there. The interior organization is perfect for stowing cards, keys, and devices, and it keeps everything separated but easy to spot. The price is steep, but we've seen it dip below $200 before.

I was a fan of Savage Industries' EDC One bag, but 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.

When I first saw this bag, I was skeptical. I've always had mixed feelings about vertically oriented messengers. They have a bad habit of banging against my hip when I walk, or of being really awkward to cinch closer to my body. 

Waterfield's Muzetto crossbody shares the sturdy construction of its bigger sibling, but it has fewer internal pockets and the leather doesn't have as much give, so stuffing it with bulky objects, like full-sized headphones, can be awkward. The big weighty front flap secures seamlessly (and quietly) with a magnetic closure, and it flips over the back and rests securely against your body if you're walking around with it open. That's something I never thought I'd want to do, but reaching down to pluck out a camera, a sketchbook, or my phone makes it feel like an assistant is handing me the things I need. 

Because it's vertically oriented, there's much less risk of your stuff spilling out onto the sidewalk if you crouch down to take a photo. It's the perfect bag to take to a museum for an afternoon, perfectly sized for a sketchbook and pencils, and the whisper-quiet magnetic closures make it super discreet. Nobody wants to open velcro in the reverential hush of a museum. 

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.

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.

The Bellroy Sling 7L is the first hands-free sling I've absolutely fallen in love with. It's big enough to carry some essentials (keys, masks, hand sanitizer, phone, wallet, and sunglasses) with room to spare, and because of its slim and flat profile, it doesn't feel bulky, no matter how much you pack in there. It sticks close to your body and swings around to the front with ease, making it a great choice for everyday use in a world of social distancing. It's small enough to feel unobtrusive but expansive enough that you can fit everything you need.