Filson 256 vs Filson 258: Which Briefcase is Right for You?

Filson, a brand renowned for its enduring quality and classic elegance, has been at the forefront of crafting superior products for more than a hundred years. Among their extensive array of offerings, the Filson 256, Filson 257 and Filson 258 bags are particularly noteworthy. Celebrated for their tough build, visual charm, and practical functionality, these bags have earned their reputation. However, the Filson 257 has been discontinued as a bridging product between the 256 and 258, check out my review of the 257. The question, then, is how to decide between these two remarkable options? Our comprehensive comparison is here to answer that question. In this article, we’ll explore the features, pros and cons of the Filson 256 and Filson 258 in detail, guiding you in making a choice based on your specific needs.

Filson 256: The Classic Choice

The Filson 256 is the original size of the Rugged Twill Original Briefcase. It measures 16 inches wide x 12-1/2 inches high x 4 inches deep and has a 13 liter capacity. It is made of 22 oz. cotton twill that is water and abrasion resistant. The briefcase also features bridle leather handles and straps as well as brass hardware and zippers.

The Filson 256 offers a practical design with a zippered main section spacious enough to house a 15-inch laptop along with your papers, books, and daily necessities. Designed with efficiency in mind, it features two extended open pockets on both the front and back, plus two internal dividers that make grabbing your notebook or computer a breeze. For those on the go, an adjustable, removable leather shoulder strap with a padded section ensures you carry in comfort.

Thinking about a compact yet classic briefcase that can stand up to daily wear and tear? The Filson 256 fits the bill. It’s not just a perfect companion for daily commutes or casual work environments, but also a trusty travel ally, neatly fitting under plane seats or in overhead compartments. Plus, its ageless design complements any look, making it a versatile choice for any wardrobe.

Some of the pros of the Filson 256 are:

It’s so light you’ll hardly notice you’re carrying it. Room for your laptop and everything else you need? It’s got that. It has enough space for daily work and study use. Rain or shine, it’s built to last with water-repellent durability. Its design is as uncomplicated as it is stylish, simply elegant.

Some of the cons of the Filson 256 are:

It lacks a cushioned spot specifically for your laptop. For some, its size might not fit the bill, and initially, its stiffness might catch you off guard. While its quality is undisputed, the price tag may be a bit steep for some. There are great alternatives to this compact briefcase, such as a backpack may be a more comfortable alternative. The 256 briefcase is missing the snap hand grip, making its hold less comfortable compared to the 258, which offers a better grip.

Filson 258: The Padded Option

The Filson 258 stands as the big sibling in the Rugged Twill Original Briefcase family, stretching out to 16-1/2″ in width, 14″ in height, and 7-1/2″ in depth, with a roomy 22-liter capacity. While sharing the same quality materials as its counterpart, the 256, the 258 adds a little extra, sprinkling in some additional features that set it apart.

The Filson 258 briefcase is equipped with a two-snap hand grip on the carry handles, spreading the weight across your hand and keeping the handles in perfect alignment. Four full-length compartments provide ample space for essentials like documents, books, clothes, or other items, all shielded from rain and dust by a snap storm flap over the zipper.

One compartment even gets an upgrade with foam padding, making it perfect for protecting your laptop. The zippered front compartment is a handy organizer, with special slots and pockets for things like pens, phones, chargers, or tools. Carrying is a breeze with an adjustable, removable leather shoulder strap padded for comfort. Unlike the 256, where the shoulder strap attaches directly to the canvas, the 258 uses a large leather baseplate. This design spreads the weight across a greater surface area, letting it carry even heavier loads.

Filson 258 and Filson 257 baseplate

If you’re someone who demands a lot from your bag, the Filson 258 could be your ideal match. It’s up for anything, whether that’s traveling, camping, or working in rugged conditions. Not only does it hold a surprising amount without losing its shape or structure, but its tough, masculine appearance makes it the perfect companion for the adventurous among us.

Some of the pros of the Filson 258 are:

With its fully foam-padded compartment, the briefcase assures protection for your delicate items. Space is aplenty, and the extra zipper pocket means room for everything you need. For carrying comfort, a two-snap hand grip has been added, and durability hasn’t been neglected either, with water-repellent materials that promise to stand the test of time. All of this is tied together in a design that’s both sturdy and solid, built to withstand whatever comes its way.

Some of the cons of the Filson 258 are:

The weight and bulk of this briefcase may be a bit much for some, especially in certain situations where a lighter, more compact option would do. It’s not for everyone, and in fact, some consider the Filson 257 Computer Briefcase a great alternative to the 258. They appreciate it for being less cumbersome and heavy, yet still offering plenty of functionality.


When it comes to lifetime quality, both the Filson 256 and the Filson 258 briefcases are hard to beat. Crafted from top-notch materials and adorned with a classic and unending style, these two have a lot to offer. But subtle differences might tilt the scale in favor of one over the other for your particular needs.

If simplicity and elegance define your style and you want something light for daily use, the Filson 256 could be the one for you. Perfectly sized to carry a laptop and the essentials, it manages to stay unimposing and versatile.

On the other hand, if your lifestyle demands more space and robustness, the Filson 258 might be the better fit. Beyond its ability to carry your laptop and numerous other items without compromising its shape, it’s designed with comfort in mind. Features like a foam-padded compartment and two-snap hand grip add convenience, and its rugged appearance is a perfect match for the adventurous.

Your preference between these two will likely boil down to personal taste, specific needs, and perhaps budget. Both briefcases have the quality to serve you well for years, and choosing between them might just come down to your unique lifestyle and taste.

We trust this comparison between the Filson 256 and Filson 258 will guide you toward the right decision for you. Should you have further questions or insights, your thoughts are always welcome in the comments below.

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Stan is an adventure enthusiast with a love for the outdoors and American heritage brands like Red Wing and Filson. With a background in environmental science, Stan combines his outdoor experiences with a commitment to sustainability. His reviews go beyond functionality, exploring the brand ethos and craftsmanship. Stan inspires readers to choose gear that's durable, environmentally responsible, and true to American craftsmanship, making his advice indispensable for outdoor aficionados.

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