More Baggage

The Famed Filson Briefcase as carried by the author for over a decade.

In the comments, the Filson briefcase got a lot of exposure.  I carried one for 10 years +.  That’s good, but then again…


Maybe I am being to harsh here. If it weren’t for the shirt. Well, and the sunglasses. And the Yankees hat. Go Sox.


I carried one so much that I added an ACK patch to it.  ACK are the call letters for the Nantucket airport, which is incredibly bougie EXCEPT I’ve been going there for 30 years, even when I was poor.  I have Nan-Cred.  Anyway, let’s talk the bag.  First thing is obvious, it can take a beating.  This bag saw a dinner with Trump (REALLY funny story he told – don’t be a jerk and make this political, the story he told was a really good one).  It saw the first concert I played in 15 years, it saw a ballet dancer I would really rather not talk about, it flipped itself over in the same truck I flipped myself over in, and it saw the inside of a commuter train.  The more I beat it, the better it looked.  Here’s the back:

Rear View

If you are looking for a bag that can take the years and the leather holds up (if this were a decade ago there is a really good joke that goes here) the Filson is your bag.  BUT.  If you are looking to carry more than a few things, this bag is a challenge.  I carry a lot.  I carry a Midori Traveler’s Notebook with me everywhere, it doubles as almost everything.  I carry a number of pens.  The UniBall Air because it writes like a fountain pen and if I flip another truck it will write while I am upside down, a few fountain pens because at the end of the day everything looks better written with a fountain pen, a multi-tool (I swear to God the day you forget the multi tool is the day you need it), I carry band-aids and super glue (the two are not related).  I carry big headphones because nothing in your ear sounds anywhere near as good as anything over your ear.  I carry a laptop AND an iPad (the laptop is for work the iPad is for everything else).  I carry one real book (The Gold Coast by Nelson DeMille which is simply the best novel ever written) at all times because I have been burned by drained batteries in the past.  I carry a spare battery for the same reason.  I carry a spare ballcap because it rains and I lose umbrellas.  Every. Single. Umbrella. I. Buy.  I carry a spare pair of reading glasses, I carry a spare pair of sunglasses.  And so forth.  All of this is organized like I was an engineer, that isn’t the problem.  But fitting it all in this bag is a hardship.  The bag has a key fob, which is great, and pockets, also great, but even so.  If you carry stuff, this is a hard bag to work with.  But that is not the worst of it.  The worst of it is –

This. Which is the same as…

I would have married this bag if it weren’t for the teeth.  (Again, a decade ago…)  I would have found room somewhere else.  I would have tried to make cargo pants Ivy.  But every time I reached in the bag, the zipper, which is actually a FEATURE,  a FEATURE,  they EMPHASIZE it, every time I reached in the bag I left DNA.  And I worked that bag.  You can see from the pictures.  I worked that bag hard.  The zipper never let up.  Brooks carried this bag for a minute, and I am betting they got the same feedback.  It fits great, you can wear it or carry it.  It will outlast you.  But, as Fleetwood Mac says,

You will Bleed To Love Her.

Which is why I went all 70’s with the other most coveted bag, the J. Peterman Counterfeit Mailbag.  Here’s mine:

Soft. Easy. She’s a lover, not a fighter.

I will say this before I say that.  I never get as many compliments on much of anything as I do on this bag.  From everyone.  It is a statement.  And man, it is easy to get in to.  (A decade ago…).  One flap, and there is a very soft button hook you can use if you want.  The leather is soft, the strap is soft, the body is cavernous.  It has a zipper pocket on the outside too, if you feel you want something protected a little bit.

Which is why it kills me that they messed it up.  How?  First, the strap.  It is a thin strap, ok fine, I will live with that.  But it is also about a foot long.  More than that, I mean, you can carry it over your shoulder, but you cannot cross body it.  Which if you are a bag wearer as much as you are a bag carrier, is a disqualifier.  You can carry it by the handle, but that is not balanced.  If, for example, you were carrying a magnum of wine AND a spare shirt for tomorrow morning to an apartment you were invited to that you might not make it out of til morning, and you had to walk a few blocks because god forbid they live near a real parking garage, this bag would be lopsided and your shirt might look like it was trying to get out.

That, and the inside of a messenger bag without pockets (yep, no pockets) is a black hole.  You can get the wine out, but if you threw a pen in there, you are gonna fumble.

Next week,  bags that actually work.


10 Comments on "More Baggage"

  1. Great post. I’ve carried a green Battenkill briefcase from Orvis for years. It’s
    never let me down and never failed to draw compliments.

  2. I love that product as well. My Orvis Businessman’s Briefcase has finally given up the ghost after 19 years of intensive travel use. Just ordered a new one and it will be interesting to see if this version is as hardy as the original one.

  3. Evan Everhart | November 12, 2021 at 12:06 pm |

    Take that Peterman bag to a cobbler and have the strap replaced with something more appropriately proportioned and to yr own specifications. You can even have a divider added as a fabric liner if yr cobbler is competent. Hint, use a cobbler who specializes in women’s shoes. My suggestion for best briefcase is the U.S. Army officer’s briefcase. Ill look up which model, I always forget. Anyway, Ive got one, I love it. Its handsome, sturdy, well made, has multiple compartments and is roomy enough to almost function as a minimalist overnight bag.

  4. Filson bags are ivy to the core. Like an OCBD, a Persian rug or a Barbour Beaufort they develop character and improve over time.

  5. I chuckled several times in recognition while reading this one. Much empathy for you and anyone else who has suffered the vexing logistical issues brought on by bags that are almost perfect but not quite. That’s literally every piece of luggage I own. (Yes, I am referencing a Shel Silverstein poem for children here: The persistent, though mild, dissatisfactions of its protagonist mirror how I feel about almost every article of menswear, accessory, or bag, ivy-approved or not, that I covet or already possess.)
    I eagerly await the post featuring bags that actually work. At long last, will there be a handsome and utilitarian piece of everyday luggage thoughtfully designed for the things people actually have to lug around these days?

  6. Paul Desmond | November 12, 2021 at 4:13 pm |

    I’ve been digging these last few posts. I had a messenger bag with copious pockets that my dad gave me years ago that I used in high school during a “i’m like hip” phase. People called it a murse, and after a school year quietly retired it. Now I wish I had kept it…

  7. Twenty five years later my Orvis (Gokey) “Battenkill Briefcase” perseveres and presides. They retired it. These are similar:

  8. * thirty years later, actually. Amazing.

  9. I had a Filson 256 briefcase for about a decade which gradually became too big for my everyday carry. Sold the 256 for the newer Filson compact briefcase which is now the perfect size. Highly recommend this smaller Filson briefcase. Color wise – I’ve owned tan and navy and I like tan better. I also own a tan Filson tote which I love.

  10. Try the Filson 24-Hour Tin Cloth Briefcase, change the strap to the bridle leather and you’re all set. Works well for me carrying laptop, charger, headphones, leather portfolio with legal pad, Cross pens, pewter kidney flask, zippo, leatherman free p4 in leather sheath, etc.

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