Make Your Next Work Bag a Briefcase

The Stuart and Lau Cary convinced me that a briefcase can maintain a classy aesthetic without going full Wall Street. It’s mostly made of a tear-resistant nylon — waterproof thanks to a rubber foam backing — with a canvas-like feel that’s sturdy yet soft. The Cary’s full-grain leather handles and trim are even softer, and give the bag a welcome dash of elegance, making it even more versatile. And its abundance of pockets and pouches make it the perfect companion for long commutes and traveling.

But don’t let the Cary’s understated look fool you. This deceptively functional bag is packed with features that feel more useful than gimmicky. The leather straps below the handle on the back of the Cary, for instance, have loops that you can stick an umbrella or sweater through. Behind that is a pouch that goes the full width of the bag and is held together by a magnetic clasp that provides a satisfying click when closed. Inside that is a single pocket where Stuart and Lau included a packable tote — handy if you need extra storage in a pinch. There’s also a closed pocket where you could store some documents or your favorite magazine, plus an opening for you to slide your luggage handle through. On the front are three pouches for storing items you may want to grab without opening the entire bag (travel documents, a small notebook, sunglasses).

The bag’s main compartment is just as useful. It has a total of seven pouches and a hidden AirTag pocket, plus a removable laptop sleeve that holds computers up to 15-inches and feels nicer than the ones you can get at Best Buy or the Apple Store. I managed to fit two paperbacks, aTraveler’s Notebook, and my overstuffed pen case all in there and still had room to spare. You could easily swap the paperbacks for a large pair ofnoise-cancelling headphoneswithout the bag getting bulky. Even with every compartment filled with something, the Cary avoided feeling overstuffed.

Waterfield Designs — a brand I’ve long been fond of — has a knack for crafting leather bags that look at home in the conference room or working at a cafe. The Lexington is made of a full-grain, distressed leather that’s eye-catching out of the box, but develops a gorgeous patina over time that gives each bag its own unique look. Even the scratches and scuffs my bag has picked up give it some much welcome character — it looks like it’s accompanied me on as many adventures as it has trips to the coffee shop. To add to the explorer aesthetic, Waterfield Designs uses an actual paragliding buckle to keep the Lexington’s front pocket closed — it’s both secure and fun to play with.

Unlike the Stuart and Lau or Topo Designs briefcases, the Lexington only has one compartment other than the front pocket. Inside, there’s a laptop sleeve that can hold devices up to 16 inches, plus a smaller sleeve for holding a tablet or some documents. There are also two mid-size pouches for holding smaller items, three pen slots, and a water bottle sleeve. But despite not having all the organizational features of the other bags I tried, this bag can carry a day’s worth of stuff without any problem — it holds everything the Cary can, though you have to be a bit smarter about how you store everything. When fully stuffed, the bag retains its shape, and the thick leather handles make it easy to hold without any strain. And if you need to carry it cross-body, Waterfield includes a shoulder strap to turn the briefcase into a messenger bag.

A welcome detail: like the bright yellow interior of Topo Designs bags, the gold fabric that lines the Lexington’s main compartment makes things easy to see while giving the inside of the bag a distinct look. It’s not as vibrant as Topo Designs’ yellow, but that helps add to the Lexington’s polished aesthetic.

Where the Cary toes the line between fancy and casual, the Topo Designs Mountain Cross Bag completely ditches formality in favor of an outdoorsy aesthetic. It’s loaded with pockets, zippers (complete with knotted pull cords) and buckles that give it a uniquely rustic, outdoorsy charm. The whole bag is made of recycled nylon of varying thickness and like Topo’s other bags comes in several multicolor options that add a little more pop than the neutral colorways that briefcases tend to come in. It’s also the smallest of the bags I tested, though it can still hold a significant amount of gear.

The front of the bag has multiple loops for you to hook things onto using a carabiner or other clip. And like the Cary, there are three open pockets, though the ones on the Mountain are shallower and a bit narrower. There’s still enough room to hold a phone, small notebook, or sunglasses, but not a Kindle. Above that is a zippered pocket — lined with a bright yellow nylon fabric that makes it easy to see your items — that’s deep enough to hold two paperback books. Behind that are two larger compartments where you’ll store most of your items. One has a zippered pocket inside, while the other has two mesh pouches for storing small trinkets. There’s also a dedicated laptop compartment that can hold devices up to 14-inches. That’s smaller than other briefcases I tested, but it’s a fair trade-off to get a bag with an overall smaller footprint.

Despite its compact design, the Mountain Cross can still hold a reasonable amount of items. I managed to stuff two paperback books, my Traveler’s Notebook and overstuffed pen case, a largepower bank, some wireless earbuds, and an 11-inch iPad Pro with a Magic Keyboard, into the bag without it getting too hefty or losing its shape. And if you want to carry a bulky item like a yoga mat or sweatshirt, you can attach it to the bottom of the bag using the two permanently mounted straps.. And even with all of that packed inside, the handles on the Mountain are strong enough to comfortably hold it all at your side.

Strategist-belovedbrand Tom Bihn is known for itsutilitarian bagsthat pack an impressive number of pockets and other features into sleek, comfortable designs. But unlike some of the company’s other bags, the main appeal of the Founder’s Briefcase isn’t its abundance of pockets or ability to latch endless accessories onto it. Instead, the magic of the Founder’s briefcase is in its simplicity.

The look of the Founder’s Briefcase — which is made of a soft yet tough nylon — lies somewhere between the formality of the Cary and the ruggedness of the Mountain Cross. Its front panel is understated, with only two small zippered pockets and fabric accents to create a retro, dual-tone look that wouldn’t be out of place in a 70’s travel magazine. While that look may not be for everyone, it doesn’t scream “lives in his email app” the way some more traditional briefcases do. I’m a fan.

Many briefcases feature a bucket design, wherein the U-shaped main compartment only opens partially. The Founder’s Briefcase, on the other hand, utilizes a clamshell design, so you can lay the bag flat and open it up like asuitcasefor quicker loading and unloading. That makes it easier to fit large items like a sweatshirt without having to just stuff them down into the bag, but it also makes for fewer organizational components since the bag isn’t divided into sections. On one side is a single zippered pocket up top that can hold a Kindle or iPad Mini, plus a mesh pocket along the bottom that’s divided into three compartments, three pencil slots, and a pocket where you can store your phone or wallet. Other than that, the only other organizational feature is a padded laptop sleeve that can hold laptops up to 16-inches — but you can’t remove this one to use separately like Stuart and Lau’s.

I’m on record as being a big fan oftotepacksthanks to their convertible nature. The Global Briefcase is equally transformable, but goes between a backpack, messenger bag, and briefcase, with just a few adjustments. Like the Mountain Cross, this bag sports a rustic design that wouldn’t be out of place in a coffee shop or an office with a lax dress code. It’s made of a sturdier, thicker nylon than the Mountain Cross, but is still soft and pleasant to touch. It has the chunky zippers and pull cords that are characteristic of Topo’s bags, and make it easy to open and close each compartment.

Of all the bags I tested, I’m most fond of this bag’s front panel organization. It has two large, zippered pockets (lined with the same bright yellow nylon as the Mountain Cross) that have enough room for a few small notebooks, ane-reader, or a power bank. Although you lose the sleek look of bags like the Lexington or Cary, I enjoy the added utility of the extra compartments. Behind that is the main compartment, which is totally open — no pockets or pouches — and has space for two paperbacks, my Traveler’s Notebook, a loaded pen case, and a large power bank, with some room to spare. The bag also has a dedicated laptop compartment with a little extra room for smaller knickknacks. And similar to the Mountain Cross, this bag has several loops for you to clip things to, as well as straps for storing a yoga mat, umbrella, or sweatshirt.

You can hold the Global like a briefcase — it has a single top handle — but there are also two straps that turn the bag into a backpack. To do so, you simply pull the straps out of a pouch on the back of the bag and clip them to two loops on the back. When not in use, though, there’s no way to seal the pouch that stores the straps, so they aren’t totally secure. And if you want to use it as a messenger bag, Topo Designs included a shoulder strap that you can attach to the bag as well. There’s enough padding to comfortably wear the bag in messenger mode for long walks, and it’s compact enough that you can fit it in the bag when not in use.