Your Briefcase is Probably Terrible

So many things wrong with this picture.

The briefcase is as important a part of the lawyer’s image as the traditional suit and tie, using big latin words to express simple concepts, and yelling “OBJECTION!” Think about the name for a moment — “briefcase” — it’s because we lawyers needed something to carry our reams of important lawyerly documents around.

And the need to carry things around is never ending. From the first day you first step into the law office, to your last day appearing in court before your peaceful, non-lawyerly retirement, you will have to schlep files, yellow pads, pens, laptops, and legal tomes around with you to Court, to client meetings, and to take work home with you. I can’t see this requirement of our job going away soon, no matter how much technology invades the courtroom.

With that in mind, it’s worth it to invest in a high-quality briefcase early in your career, because that one briefcase can last your entire legal career (or longer). Remember durables? Here’s a succinct way to put it: Buy the best, cry once.

So let’s talk about how terrible your briefcase probably is, and give you three potential options to replace your sad sack.

Signs you’re doing it wrong

If you are using any of the following things to carry your lawyerly stuff, you should stop, now.


Backpacks are for children. You’re an adult. You’ve worked hard now through law school, and passed the bar, and now have some fancy letters after your name. People come to you for legal advice, and it’s your duty to zealously represent them. Do you think that you, a lawyer, carrying your important client files around in a backpack like a 5th grader will inspire confidence that you’re a competent, confident professional?  Burn the backpack.

Messenger Bag

Messenger bags are for bike messengers, mailmen, and people who are too cool for backpacks. Yes, I understand that you may have a super-cool limited edition color-way bag featuring a screen print by your favorite street artist, which you really love. That’s fine, but save it for carrying your things when you’re not lawyering.

Black Ballistic Nylon Laptop Bag

The Wonder Bread of briefcases, nothing says “I don’t care” like a generic black ballistic nylon laptop bag used as a briefcase. I don’t think that anyone actually buys these — they just kind of show up in peoples’s houses, like they’re brought in the night by the Black Ballistic Nylon Laptop Bag Fairy. I like to imagine that people carry these only because they don’t have to think — they find this bag in their house, shrug, and start using it as a briefcase. They are ugly, boring, and generic. The ballistic nylon will not age well, and the zippers will likely break.

Leather Bag from “Brand Name Designer Men’s Store”

There’s a distinct  important difference between a branding and quality. Too many “designer” men’s stores these days produce garbage, stick their label on it, and charge a premium for the brand. Don’t fall prey to the siren’s song — most times these goods are made of inferior materials with inferior construction and aren’t worth the price tag. Jordan used to have one of these, and even he admits it was garbage. Save your money.

Now that we’ve figured out what you shouldn’t be carrying your important lawyerly stuff in, we should discuss some better options.

Three Examples at Three Price points For Your Lawyer-Document-Schlepping Needs

Here, I’ve provided three different options for a briefcase that will last you your entire career, and probably even longer. These are built so well that you’ll probably be able to give them to your kids, and them to their kids too.  Note: I am not getting paid to endorse any of these, but I gladly accept bribes.

For the More Rugged, Laid-Back Lawyer — The Filson Original Briefcase

Screen Shot 2013 02 08 at 08.37.06 AM 640x397 Your Briefcase is Probably Terrible

The Filson Original in Tan. Made in the USA.

The Filson Original Briefcase is a classic no-nonsense design. It’s made of water resistant cotton twill and should be large enough to handle your legal-sized files. Big, brass zippers aren’t going to jam and break. It also comes with a bridle-leather shoulder strap, in case you dont feel like schlepping it around in your hand all day.

It’s affordably priced at $225, and available in Tan,  Otter Green, or Brown.

This maybe a bit too rugged for you? Take a look at Filson‘s Leather Field Satchel instead.

For the No-Nonsense Utilitarian — Saddleback Leather Large Classic Briefcase

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Saddleback Classic Briefcase — 100 year Warranty.

The Saddleback Classic Large Briefcase is a beast. It’s made of thick full-grain boot leather and weighs in at a substantial 7 1/2 pounds. The large size is 16″ wide, a 12″ tall, and 9″ deep —  big enough to hold a redwell or two, plus your laptop, plus a few books. The pockets on the outside are great to hold extra pens, your business cards, your keys, or a bottle of hand sanitizer. Because it’s full-grain leather, it develops a wonderful patina as it ages. It will get scratched from time to time, but those scratches buff out with a quick brush and add to the character of the bag. 

Finally, because it fastens with buckles, there’s nothing to break or fall apart — you won’t have to worry about dainty locks or forgetting a tumble lock combination. The large bag with a pigskin lining is available in four different colors, and will cost you about $610.00. The large bag too big for you? Consider a medium bag or the Round Sachel. Jordan and I each use these in our practice. To the left is Jordan’s Coffee Brown Large Briefcase, to the right, my Chestnut Brown Satchel.

SaddlebackBags 640x640 Your Briefcase is Probably Terrible

The arsenal.

For the Lawyer with a Large Budget —  Swaine Adeney Brigg Westminster 3 Legal Case (American Format)

Screen Shot 2013 02 08 at 09.40.05 AM 640x496 Your Briefcase is Probably Terrible

250 years of British Craftsmanship. One amazing case.

So you’ve recently come into a bit of money and have a $2,200.00 budget for a briefcase? This Swaine Adeney Brigg Westminster case is for you.  SAB is an English luggage and umbrella manufacturer that has been around since 1750. They have held Royal Warrants since 1893 for their goods — if they’re good enough for English Royalty, they should be good enough for you.

Available in four colours (Black, Chestnut, Havana, and London Tan), this bag is made of leather tanned with natural plant extracts, rather than harsh synthetics, so it will only look better with age. It’s not as large as the Saddleback, and it costs 10x as much as the Filson, but if durability and timeless style are your things, and you have some excess cash to spend, you can’t get much better than this.

Reports from the Field

I want to hear from you attorneys out in the field. What’s your go-to bag? How has it served you? Is it something you’d be proud to pass onto your kids as an heirloom, or do you see it just as a sack to move your documents around?

If you have other recommendations at other price points, let us know. But if you want to brag about how great your nylon backpack from 7th grade still is, go start your own blog.

Until next time.



  • Tori White

    Love the points–image is everything until it isn’t. I’m interested in options for women. Also, I’m limited somewhat in mobility. Any options for those of us who’d like to pass the image test but can’t shoulder (forgive the pun) the shoulder straps? I’ve invested in a rolling computer bag but it’s too much for quick court appearances or schlepping to client meetings.

  • Sam Glover

    What does it say about my style that I hate all the bags you posted? Then again, I usually don’t carry a bag at all. I rarely need more than my iPad and a pad of paper.

    • static

      I posed your question to David Boies. He responded, “Sam who?”

      • john_d

        Ask David if he’ll do a guest post.

        • static

          I asked, and he said “guest what?”

    • Leo Mulvihill, Jr.

      Sam, I’ll tell you, but my hourly rate for therapy sessions is rather high.

    • Chris Bradley

      Sam, is “static” something that pops up by default, or do you have to type that in?

      • Sam Glover

        It is this commenter’s handle of choice.

        • static

          Second choice. My first choice was “Matthew Salzwedel,” but I thought that might prove confusing.

          • Sam Glover

            You can use whatever nom de plume you prefer, as far as I am concerned.

            • Hitler did nothing wrong

              You sure about that?

              • Sam Glover

                I’m sure you can come up with something I wouldn’t allow, but this is nowhere close.

                • Matthew Salzwedel [not really —Ed.]

                  For the record, that wasn’t me. Even in jest, that’s not somewhere I would go.

                  • Sam Glover

                    Oh, I know. (I get to see IP addresses, and I know exactly who it was.)

  • john_d

    It’s telling that the best attorneys I know pay no attention to their bag choice. Nothing is more embarrassingly funny than an attorney who steps up wearing a French cuff shirt, designer suit, and caring a $1,000 briefcase and turns out to be an empty suit. Make sure you have the substance down before you work on the style.

    • Leo Mulvihill, Jr.

      Naturally, but since this is a men’s style column, it made sense to, you know, address the style part.

  • Laura Toledo

    You can’t hate a guy who brings this to the table:
    (couldn’t help myself – apparently, there is a bacon festival in Iowa?)

  • Daniel Glad

    The Saddleback in person is way too rustic, and it looks like something deep in the throes of mid-life crisis carries around to prove he still has adventure in his bones. (Because he can’t afford the sportscar or arm candy.) My money is on something more like this for the mid-range price point:

  • Matthew Salzwedel


    Thanks for this information and the entertaining prose. What are your thoughts on buying vintage briefcases on eBay et al and then bringing them back to life by restoring the leather over time?

    There are some beautiful full-grain briefcases from the ’60s that you can pick up awfully cheap. And I like them because they already have some miles on them.

  • Grant

    I like to carry the Hartmann briefcase I picked up for $6.00 at a thrift store a few years ago. Bags like it but in better shape — no scratches, a working clasp mechanism — sell for $400.00 and higher on eBay. Sadly, it dates from the days before reasonable-sized cellphones (the phone pocket inside is for a phone that’s post-brick, but pre-Razr) and doesn’t really serve for a laptop.

    But still. Hartmann. And yes, I know you only ever see me using my backpack.

    • Patrick

      I also have a thrift store briefcase that I picked up for under ten bucks (along these lines: ). Its full leather, fully functional and cheap.

      • Matthew Salzwedel

        Yep, that’s what I was talking about.

        Mine is similar to that case, though it’s an American-made case manufactured in 1906s by Prescott Brown. Deep-buff-cowhide. $30.00.

  • Kristi

    Can’t help it, I’m a sucker for free schwag. My lugger of choice changes by the week depending on what latest conference I’ve attended (proof that I keep up on my CLE; same way I get most of my pens), what client has recently dubbed me worthy of their logowear (depending on where I take it; ditto the pens), and what non-profit campaign I may be supporting (though those never go to court; thank goodness I never have to buy pens!). And while the trendy borderline disposable grocery getters are not cool, I’m all about using them to take files home with me.

    PS ~ Can somebody email my mom these links so she knows what I REALLY want for Christmas next year? Oh, and don’t worry, I wear FABULOUS shoes to make up for the free book bags ;-)

  • Fred A. Cohen

    I have to differ about black ballistic nylon bags. Tumi makes a great one, priced at $395, which I use, and which clients have complimented . It is several years old and literally looks new.

    • Leo

      But it still looks like ballistic nylon.

    • Sam Glover

      I like my Tumi briefcase, too. It really dresses up my hoodie and Chucks.

      • Leo

        I think it’s the other way around.

  • Paul

    I got a nice briefcase that thankfully doesn’t look like any of the three pictured ones. That style of bag did not excite me at all. Mine is a Jack Georges bag although sadly it doesn’t fit my massive laptop.

  • Jon

    None of those choices are particularly attractive. I know the saddleback brand has gotten trendy recently, but I would have to agree that they look too rustic for lawyerly endeavors… like you grabbed the saddle bag off the horse you rode to the court house. Perhaps they are better suited for architects or engineers. Also, with the shoulder strap on the bag it looks less like a briefcase and more like a glorified messenger bag/man purse.

    • Leo

      1) horses for courses
      2) you can carry them in your hand and not use the strap.

  • Louie
  • Scott

    I have a “Black Ballistic Nylon Bag” by Briggs and Riley (Executive Rolling Catalog). It is more useful, better looking and more expensive than the sacks you suggest above. It rolls too. I have been rolling it around for about 7 years now.

    I have had more traditional lawyer bags in the past like a Hartman. Expensive, looked great on the shelf but a ridiculous mess after only a few years of service.

    I think it’s comical that you suggest bags that I routinely mock when I see lawyers carrying them.

    • Leo Mulvihill, Jr.

      A high quality leather bag, made of top grain leather, develops a gorgeous patina as it ages. It ends up with a character that makes it uniquely yours.

      Even the canvas that Filson uses ages well.

      But a black ballistic nylon bag is ugly on day one and will be ugly when you stop using it. It has no character.

      If you think that black ballistic nylon bag looks better than a well worn and cared-for leather piece, then I can’t help you.

  • Robert

    If you’re in the market for a new briefcase, try Etsy. I bought a handmade leather briefcase there that is one of a kind and will last almost forever. And at $250 it cost considerably less than the briefcases suggested here or found in stores.

  • Aaron Fletcher
  • Jeremy Parsley

    Am I the only one who doesn’t like the bags and prefers the hard-shell type?

  • FreddieKrueger

    And all of the bags are available at “Butt-Ugly Bags R Us”

    No thanks, I’ll continue to use my very traditional leather briefcase. My iPad slides into the middle zippered section, and the look says ‘classic’ ….

  • Mark

    Spade. Jack Spade.

  • David K. Hiscock

    Fail, fail and fail.
    Sorry; I like most of your material, but you’ve missed an important point about the bags you’re recommending.
    All have the “must be buckled up to work” strap on them.

    Please consider a very small design difference that makes a WORLD of difference – TWO handles that match up, clasping in your hand, the bag works great whether you buckle it or not.
    I almost never do.

    Next suggestion – the bright-shiny new bag just screams “graduation present”.
    Pick up your bag at an estate sale/garage sale/tag sale/pick your regional term and insert it here…

    Back when I had hair and was sorta cute, it was hard to be taken seriously until the judgment was presented (then I had to do it all over again, because insurance companies don’t learn very well)
    Since I got gray, lost most of my hair and nobody in their right mind would call me cute, when I show up with a bag that has some scuffs on it, there’s a better chance a person will consider what I say to be “voice of experience”.

    Not offered as a trolling volley, a sincere opinion.
    Not my bag, but an example of what I’m talking about:
    I certainly didn’t get *my* bag at Barneys or pay $1,800, but yeah, the nylon backpack or the messenger bag is a) not gonna last and b) not saying good things about you.

    All respect – David K. Hiscock
    Mediation, Arbitration & Trial Solutions

  • Jack

    All of the above look pretty frumpy to me. I have two bags. One, for every day, is a black leather briefcase in classic Italian style, sort of similar to the arsenal, but it’s not so thick — probably maxes out at about 2 reams of paper, and has a button latch instead of a buckle, and no additional side straps. Pretty similar to this: I bought it in Italy the year I graduated from law school — 10 years ago, with the idea that I’d keep it for my career. So far so good.

    My second go-to bag is the most boring and utilitarian bag there is: A classic litigation bag — basically a box with handles. No ouside pocket, no wheels, no strap. The design is exactly like this one: It is high quality and was handed down to me. No idea whether it originally cost the inflation-adjusted equivalent of $2,100.

  • Scott

    This beast of a bag will last longer than I will. It’s in the No-Nonsense Utilitarian category.

  • m.l.

    Call me old fashioned but I would not trust an attorney’s billables if (s)he had a 2k briefcase/messenger bag. That said, I would not be able to tell the difference between a $100 bag and a $1,000 bag. I leave that to fashionistas. All it takes to earn my respect is to be smart, dedicated, and honest. If you have enough time to think about what other people might think of your bag…you’re doing it wrong

  • fer

    Leather briefcases always look better than non-leather, but they are heavier and the compartments are not always as practical or protect electronics as good as nylon bags/backpacks, plus backpacks help when carrying a lot of things. That being said my dream leather bag is this:

    I think hard cases look cool, but when you want to take out something quickly, zippers are better.

  • Phil Lowry

    I use the assault pack I was issued in Afghanistan as an Army JAG. Holds lots of paper, my machine and my iPad. Huge zippers for carrying heavy loads of ammo and gear. For court I usually just take my iPad in any event. No need for physical paper if you’re prepared.

    Think I look like a kid with an assault pack? I authorized air strikes on the Taliban. I don’t need a swanky leather thing (which is a pain to open) to validate me.

  • Joelyn Toby

    I purchased a great briefcase from Leather Tree 10 years ago and it is still perfect. I chose one on wheels that had a lot of room for all of my files. They have a separate section just for lawyers briefcases.

  • John H
    • Sam Glover

      I’m sure it’s great and all, but the images aren’t displaying for me.