Office Carry: Briefcases and Backpack

Let’s have a chat about office bags. My stance for a long while has been: wear a backpack, no one cares, they are more comfortable, and better for your back. Something like that, right? My stance is now: I care how I look more than I used to, and backpacks don’t look that good on me when I stare at the mirrored elevator doors, so carry a briefcase.

Back at my house, I was once again swimming in a sea of bags stuffed in my closet. Bags I didn’t want to sell, and yet not a single one of those bags felt like the bag I wanted to use for the office. Then I started longing after Hardgraft’s Long Haul Briefcase. It looked like the beacon, the next bag which would rid me of this feeling of not having the correct bag.

Normally, I pull the trigger, buy it, and give it a go. But when the bag price is over $800 before shipping — it makes a man stop and think about his poor financial bag investments. So I instead sat down and asked myself: what the actual fuck do I want from my office bag? What actually matters? Well, first I had to document what I actually needed to carry, and then what I wanted to carry. But after that gear-listing-detour, I came up with seven things which matter to me for my office bag — my thoughts on how I should select a single bag for the office:

Backpacks cause me to carry too much stuff.

Shoulder bags objectively look better than backpacks.

I much prefer to always carry my Leica Q2 with me, even though I don’t use it daily, so my bag must support that.

It’s really nice to be able to carry my coffee inside my bag when I want to.

The bag has to be stylish, but that style has to be a reflection of who I am (or at least who I see myself as).

Must not be fussy.

Must be able to carry two iPad Pros from time to time.

The thing about backpacks in the office is that I only carry my bag from my car to my office. That’s not a long distance at all, so carrying comfort doesn’t really matter to me. Instead, I can optimize for looks, and I much prefer the look of carrying a briefcase. If I were commuting on mass transit, or walking a decent distance to the office, I would absolutely be using a backpack (and for sure the Journeyman). But that’s not what I am doing, so with the criteria above, I ran through the briefcases I currently have, and what I was looking at getting to try and determine how I actually felt.

So close to perfection for the office, but still perfect outside the office.

Filson Original Briefcase

(My review.)

Holds everything I want but is stuffed when doing so.

The only quick access pockets are open top, which means you have to fuss to get into the bag, and fuss to not spill things out of those pockets.

Can be a little tricky to slip stuff in and out of the bag when it is this stuffed full, especially for the laptop section.

Looks really nice, and pairs well with my clothing in the Otter Green color I own. Absolutely top notch looks.

Filson 24hr Briefcase

(My review.)

Holds all my gear perfectly.

Looks a little more unkempt than the Original Briefcase.

I love using the front two pockets to easily get to some gear.

I tend to overpack from time to time with this bag becuase it affords extra space.

Which color you select should be done carefully, as each offer their own character and spin on the bag.

Sometimes I don’t really want a waxed good against my clothes as I worry about wax transfer.

Hardgraft Flat Pack

(My review.)

Barely holds even the bare minimum of what I need.

I love the feel of the bag.

I love the look of the bag, especially when it is worn.

There is no external access, it’s all one pocket.

Hardgraft Long Haul Assumptions

(I don’t have this bag, this is what I am guessing I would get out of it.)

Holds almost everything I want.

Looks and feels amazing.

Some external access for a few key items.

The leather is soft, so perhaps not as durable long term, or at the very least requires frequent leather care.

Worry it is too shallow to fit my coffee and Q2 comfortably with the iPads.

It will work against most of my wardrobe, but will also feel a bit stuffier/classier than a lot of what I wear. Will it work well with my Iron Rangers? I don’t know, I suspect not as well as the Filson’s.

Where My Head Landed

I spent a week thinking this through. I had long ago ruled out the Flat Pack and the Original Briefcase, as I knew that they were really good bags but not ideal for my current office needs. And I absolutely love the 24hr as a bag, but at the time I started this, I was on my third color of the bag in Navy, (Dark Tan first, then Cinder, then Navy) and while I love the bag, I didn’t feel at home with the color.

The Long Haul seemed like a light at the end of the tunnel for me, but there was something not quite it. And that’s when I realized that I dress more workwear Americana than I do, Espresso Italiano — yearn as I might to live in Capri.

That pointed me directly at the 24hr, and I quickly realized: I have always wanted this bag in Otter Green, as that is my favorite color from Filson, and thus my issue is with the Navy and that color not feeling cohesive with my style. Thus my issue is not the bag. So I swapped my Navy 24hr for an Otter Green version, and this is my office bag now.

I’ll still test other things for reviews, but I am no longer planning on switching bags multiple times per week, and keeping load outs I can easily swap between bags, etc., instead I am ‘moving in’ to this 24hr and keeping it that way. I don’t plan on having many days where I grab a different bag, a routine that became tedious at its best.

So why is the 24hr so good for me?

There is a lot of versatility in the style of the 24hr. It exudes character, and works well with everything I wear. The only time I would feel slightly off with it, is if I were to wear a suit. Swapping to the Original Briefcase would resolve this, and that’s a bag I plan on not selling

The 24hr carries more gear than all my other briefcases, without looking and feeling massive. It’s a little surprising how much it carries, and I don’t even use the open top pockets on it.

There’s far less maintenance needed with this bag than you do with leather. You don’t even have to re-apply wax if you don’t care to.

This bag feels like me. I can’t explain it, it just does.

There’s really no compromise when I carry this, since it can carry whatever I need/want it to carry, and it does so very easily without all the fuss introduced with the other options. It can go skidding across the parking garage, it can appear next to me in important meetings, and I can quickly and easily get to a pen — while not worrying that I lost the pen in that parking garage escapade.

So yeah, the Filson 24hr Briefcase is really good shit.