Briefcase Showdown: Filson 256 vs 257

One of the most hotly debated topics in the world of Filson, especially to newcomers, is the decision between the Filson Original Briefcase 256 and the Filson Computer Briefcase 257. They share a design aesthetic and differ by only two inches in width, but there is a bigger difference here than initially meets the eye. So let’s get started…


Both briefcases share the same basic design. They both have a zipped main compartment with a storm flap that snaps closed and they both have two full-length exterior pockets, two carry-handles and a shoulder strap. Here is how they differ…


The 257 comes from the factory with a two-snap hand grip attached to the carry handles. This serves two purposes. First, it distributes heavier loads across your hand to make carrying the bag very comfortable. Second, it keeps the handles neatly together when you place the bag down or are carrying it with the shoulder strap.

The 256 does not include the hand grip, but Filson will install it for you for $20, so if it is important to you, there is a work-around. I am in the minority, but I definitely prefer the 256 without the hand grip. I find that the two bare handles are very comfortable with my typical load and I like the casual character of the floppy handles as they break in. In addition, it makes access to the main compartment easier if you are constantly in and out of your bag.


The 256 has the shoulder strap attachment point stitched directly to the canvas. Whereas, the 257 uses a large leather baseplate to connect the attachment point to the bag. This will spread the load over a larger surface area and should allow the bag to handle very heavy loads slightly better.


The 257 has a wider base and will stand up on its own. The 256 will need to be leaned against a desk or a chair because of its narrow base.


In person, the 257 definitely feels bigger and bulkier than the 256. It only weighs about three ounces more, but overall it feels like you are carrying around considerably more bag. Whether this is a good or bad thing is entirely subjective. If you are a student and carry lots of textbooks or have a more sizeable laptop with a charger brick and want to carry a water bottle, a jacket, etc., then the bulkier 257 may be just what the doctor ordered.

It is hard to truly understand how different the two bags feel without handling them in person, but you can get a sense of the size difference in this picture.


The inside of the 256 is fairly basic. The bag has a spacious main compartment sandwiched between two full length interior pockets, one of which has six smaller pockets (of various sizes) sewn onto it for pens, business cards, calculators, cell phones, etc.

The full length interior pockets are perfectly suited for a small laptop (13″ MacBook Air), a legal pad holder or an iPad. If you want to use a 15″ laptop with this bag, you will need to put it in the main compartment.

The 257 is a little more complex inside. The following schematic (from the Filson web site) is the best representation of the interior. It starts with the basic 256 layout and adds a large, full-length laptop divider (which is not secured to the bottom of the bag) and three additional large sleeve pockets sewn to the inside of the interior pocket.

I find both layouts to have certain advantages. The 256 is simpler and cleaner and provides all the essential storage that I need for most days. While the 257 includes more pockets and dividers, they do intrude into the interior space a bit if you don’t need so much partitioning.

Because I use a 13″ MacBook Air, which easily fits in the interior side pocket, I often wish that the 257 did not have the extra computer divider so I could make better use of the main compartment. If you use a 15″ MacBook, you may need to put it in the main compartment anyway so the laptop divider may be rendered superfluous.

For many years, the three sleeve pockets on the inside of the 257 did not have a sewn bottom, meaning that they are designed to secure larger cargo, but cannot be used as conventional pockets to hold smaller items. I actually love the sleeve design because I am able to fit two 16 oz Nalgene water bottles and use the remaining sleeve for my laptop accessories.

In the last few months, I have read reports that Filson has changed the design (in response to customer demand) and is now sewing across the bottom to create closed pockets. This change is definitely something to be aware of so that you can be sure to get the layout that suits you best. My 257 was purchased locally one month ago with the open sleeves and it is my preferred layout.


You may be surprised how much the 256 Original Briefcase actually holds (I certainly was). Here is a visual representation of how I use the bags on a daily basis. Here it is full and ready for the day..

Here is a top view of the bag’s contents…

Here is an inventory of the contents and a picture of everything unpacked…

  • iPad 2 (with Saddleback case)
  • 13″ MacBook Air with neoprene sleeve
  • Leather legal pad holder
  • (2) Large hardcover books
  • 3-Ring Binder (1.5″)
  • Assorted pens and pencils
  • Magazines and catalogs

If you need to carry heavy textbooks (or more than a couple hardcover books), then the 257 may be a better choice. I would definitely recommend the 257 for college/graduate students.


Bottom Line: both briefcases are excellent, but unless you have a specific and compelling reason for the extra size/bulk, choose the 256.

CHOOSE the Filson Original Briefcase 256 if you…

  • are looking for a well proportioned bag with just the right amount of storage;
  • use a 13″ laptop and do not need to carry a lot of chargers or peripherals;
  • are having trouble deciding…the 256 is a better choice for most people.

CHOOSE the Filson Computer Bag 257 if you…

  • are a student or professor who carries multiple large, heavy text books;
  • work in an occupation that requires you to transport large binders or significant amounts of paperwork (a lawyer for example);
  • are a frequent business traveler who would like to fit a change of clothes and some toiletries along with your business items;
  • you work in the field and need to carry tools, lunch, water, or specialized equipment in addition to a computer and some paperwork.

If you have any other questions that I can help you answer, please leave them in the comments. Also, I would love to hear about your 256/257 experiences. Thanks for reading:)



  1. Dan

    Hello Charles,
    Very concise and informative review, but i’m wondering if neither of these bags are too big or bulky for someonw who’s 5.3 feet?
    I would rather have the 257 since i’m a college student, any tips?

    • Charles Page

      Hi Dan…thanks for your comment. The 257 is quite large. I am 5’10” and my wife is 5’8″ and the bag looks more like a travel bag than a briefcase when my wife carries it. However, for use as a college student, depending on your load, the 257 is probably the best size to haul larger items like a lunch, water, a computer and textbooks. How large the bag looks depends more on your frame than on your height. Choose the bag that works best for what you intend to carry…it will look great because it is a Filson:)

  2. Glen

    Very helpful info indeed. I purchased a used tan 257 online and found it was heavier and bulkier than expected ( I’d never tried the 256 ) . I’d been using Victor backpacks for year – so spoiled by lightness. I splurged on a 256 online used tan .. and can say this will be my go to bag. It’s a bit lighter, less bulky and for me easier to handle. After reading you comments on both ( I discovered this blog today ).. I can agree that each serve different purposes… and the 257 would make the perfect overnight travel bag, or one if you need to pack alot of things to go one place.. not for toting around 10 places in one day. The 257 does use up space with ‘assigned’ pockets.. and you need to already relate those needs before choosing. I did manage to use all assigned pockets.. and it kept them organized.. but the price is the extra weight and loss of other space inside on the 257. Filson would do right to tailor pocketing from a lighter and perhaps more flexible material. So, the ‘have both’ option being ideal hit home. If I need to let one go it would be the 257 … to cultivate the minimalist in me more.

  3. David Cornier

    Hello! Thanks for the comparison, its very handy! I just got a 256 at a good price and now I’m thinking it might be too small. I know the thickness is 3 inches but it seems you got more than that out ofnit, about how thick was all the stuff you put into it? I measured the stuff I need to bring on a future trip and with a notebook, textbook and laptop I’m already at 3 3/4 inches. Thanks again!

  4. dave weglarz

    Hey Charles, please keep this site going. Years later, people still come back to your posts and info. Just had to say thanks, and perhaps ask if maybe you felt like doing a 257 vs. 258 showdown?

    • Charles Page

      Thank you for the kind words…I have not added any new Filson bags to my collection lately, but I do have a few reviews I plan on posting as I travel a bit more and can give updated impressions. I don’t currently own a 258, but it is next on my list, so I will be sure to add another showdown review as soon as it arrives. Have a great week!

  5. Pingback: This Japanese Painter Bag is the New Filson 256 – Put This On

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