If I were in need of such a bag, my first stop would be the army/navy surplus store near my house.  They've got an entire section of canvas bags in every shape, size, and pocket configuration imaginable.  Not to mention, you'd be looking at like $20 - $60 as opposed to $400.  That's where I picked up my trusty over-the-shoulder college satchel that served me well for years.

There seem to be endless websites selling the stuff too.  This is the selection from the first one that came up in google. 

http://shop.sportsmansguide.com/net/browse/military-backpacks-bags.aspx?c=163

The thing about army surplus is that I want something casually resembling a briefcase with handles (and shoulder strap) that would serve me well in the city too. Something with appropriate compartments for papers and documents like a briefcase, a space for an iPad, boosk, etc. I doubt those proletarian military bags would be as practical and aesthetically they're a bit too backwoods sportsman or regimental looking. I wouldn't pay the full asking in that listing btw, a brand new Filson goes for around $350 which is about what I'd be willing to cap on.

Oliver do yourself a favor and buy your Filson brand new. If anything, the materials on the new bags are even better than before. This things are built to last and guaranteed for life. If you can wait till June get it at 40% from Brooks Brothers at their Fathers Day sale.

While the 256 is great ( i have it!) I would suggest you also look at the medium field bag, as it may be more versatile for your purposes.

The straps are great and they will break in nicely and are pure quality. Don't listen to the internet boys complaning about the leather straps - this is how a strap should be they are not used to real leather goods.

As for me - all I can say is that few people travel with more frequancy than me and my luggage needs to wistand the elements and look proper at all occasions.

Last edited by Senorservo2.0 (2014-04-14 15:01:48)

Thanks for the advice, Jose - I'm sold on it!

What makes the new materials better than the old? That's pretty exceptional for the old US catalog outfitters like Filson, Orvis, Bean, etc. It's usually all about brand cheapening and outsourcing. Kudos to Filson if that's not the case though!

I'm not wild about the look of the field bag to be honest, but I did consider the small 220 model duffel. I like that a lot but I'm not sure it'd be as practical as the 257. Do you think the briefcase might be a bit tight for the intended purpose? Also how lightweight is your 256?

I wonder if I should reconsider and just opt for the small duffel bag as a carry-on and for train travel and not carry around as much during the day...

Thanks Jose, I'm gonna recommend you for a sales comission!

Do you know the model number of the new bag by chance?

Brooks has a pretty tasty looking "olive" color that seems to be an exclusive. I think my BB card gives me an automatic 10-15% so it's probably got an edge over the new customer discount at Filson. It technically wouldn't be a first purchase anyhow as I've bought some cold weather gear from their catalog before.

Did your otter green look solid right out of the box or did it take a couple of months of wear?

I think is the new Carry-On Bag - but yeah Brooks is your best source for Filson.

257 is a classic. Their new models are hit or miss. The otter green looked good but sun exposure and wear makes them look great. I hope it works out for you, as they are great little bags that only get better over time.

Wow that was a great link. Oliver - since you the time you could check the bags at Unionmade or Cable Car C. They both carry Filson.

Hi Oliver,
I have a 257 since a couple of years and use it everyday to go to my office and on short 24 hours trips. Fabric is rather rigid and the strap is not very soft on the shoulder (I actually don't use it), but it is a great bag and very versatile. It's perfect for my 11" macbook with a lot of other stuff.
A note about the "vintage" one you linked in the first post. I'm not so sure it's a vintage one as it looks exactly as the new but distressed 257 that exists since a couple of years, these are new bags that are water washed to be distressed in this way. I know it because they are officially made by the italian filson distributor that happens to be located very close to where I live and I talked with them about it. I was thinking to buy it too, but when I saw it in real life I decided to go for the "new" one. One day I can always wash it in a wash machine to make it like the distressed one without paying the premium price. Just my 2 cents.

P.S. Oliver please contact me asap by pm or email. Thanks

I like the Duluth Trading stuff. I have the Bashful Billionaires briefcase for  a fair few years. Suits me well. When travelling overseas I just schlep around with extremely practical cheap and cheerful robust stuff. In fact last few times have got it down to just cabin carry on luggage.

http://www.duluthtrading.com/store/mens/mens-accessories/mn-bags/mn-duffle-bags.aspx