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The Briefcase Dilemma

November 30, 2025 by Anthony Sculimbrene

In the past six months my carry at work has fundamentally changed. Two things happened: first, I got a new laptop (a Mac Book Air) and I switched from paper to a Remarkable 2. The entirety of my carry, aside from a charging kit, which I will cover next week, is about as thick as the Victorinox Bantam is tall.

Together, these two changes greatly diminished the volume of what I carry on a daily basis. And while you might think that the Remarkable 2 was the bigger space saver, the laptop’s charging brick was giant and getting rid of it saves more on weight and only a tiny bit on space compared to the deletion of paper.

If I had purchased a normal briefcase, this change would probably sync up nicely to buying a new laptop bag. But I bought one of the best things I have ever purchased in my life—the Tom Bihn Cadet. This was a “slimmed down” briefcase compared to the Tumi I had. It was almost 1/3 the size. But now, the Cadet is a little capacious. Its still in great shape, even the shoulder strap, so I am forced to not get rid of it, but instead, replace it. For the record, I got my Mom a Bihn bag for her birthday around the same time and it too still works wonderfully and looks like new. I didn’t get a flukey good bag. All Bihn stuff is awesome.

But this means I have to start over. The Cadet is a 15L briefcase. I could go down to half that and be total fine. In fact, the Tom Bihn laptop sleeve, call the Cache, is only an about half too small. Tom Bihn makes a bag called the Daylight, but it doesn’t fit my 15 inch Mac Book Air. A 16 inch compatible Daylight would end this right now, but alas Bihn doesn’t make one. So this means I have to go on a search. And because this is something that happens infrequently, I thought it might be interesting to document how I do this.

The Criteria

There are things I need in this new bag and things I want. I am going to break them down here like that.

Needs

Less than 10L

This is a big one. I just don’t need that much space anymore. The Bihn Daylight looks practically perfect, volume-wise, but it is too small for a 15” laptop. Had I known it would have been this big of an issue, I would have opted for the 13” Mac Book Air, but I thought the additional screen and real estate would help with working on the road, which I do a lot. This criteria is a really tough one given the others.

Padding for Electronics

I have a Bihn sleeve and it works well in the Cadet, so I’d do that again, but a bag with padding built it would be nicer. It would make the space inside cleaner and easier to use.

Small organizing pocket

I still run with a pen and I have some government IDs in a pocket along with my earbuds and some other stuff, so a bit of organization is still needed. I am not quite ready for tote bag style carry, which is basically a fancy garbage bag.

Professional Look

There are a lot of bags and bag companies out there. Some are fashion bag brands. Others are built for use on a cattle drive. Whatever the purpose, this is a bag that will go with me to court. I love Red Oxx stuff, but it is not professional looking for my job.

Superior Strap Design

Invariably over time the weakest link in a briefcase is the shoulder strap. The Bihn Absolute strap is a revelation. Even now, 13 years later, the Absolute Strap works well. It looks a little worse for wear on the underside, but it’s still 100% functional. No other strap I have had comes close. They tangle, they bunch, they slide around. Generally the stink. Finding a good one will be very, very hard.

Fits a 15” Laptop

This is the criteria that is really putting tension on this purchase. Making something small in volume but big enough for this size laptop is really, really hard.

Wants

Rear mounted shoulder strap attachment points

This is a trend among newer, more design conscious bags and something the beloved Cadet lacks. You can see these on the Bihn Daylight. Instead of mounting the attachment points on the sides of the bag, the attachment points are mounted on the back of the bag (the side you keep next to your body). The ease of access this will provide and the fact that it means the bag can’t be wrong side out without real effort is a huge plus. I can’t tell you the number of times I have grabbed the Cadet or all my other briefcases only to realize the small pocket organizer with my keys is tucked next to my body.

Easy Access Key Device

The Cadet’s strap and hook system is great. Lots of bags have something like this, but a good one is a huge plus. Because the Cadet’s works so well I don’t carry keys anymore. Once I consolidated my wallet with my cellphone, two of the three “non-enthusiast” EDC items (keys, wallet, phone) vanished and I have not looked back thanks to the great key strap in the Cadet.

“Speed Pocket”

The Cadet’s easy access phone pocket is great. I don’t actually use it as a phone pocket anymore, but as a quick access thing for change, a few folding bills, or a building key card, it works incredibly well. This is not a strict must, but most bags now have something like this.

Fully Water Resistant Zipper

The Cadet’s taped seams, which still work, do a great deal to protect what I carry and given that they are essentially my entire office, its worth it to pay a little more for water resistant zippers. It’s not a must. I am not a marine biologist, after all, but if I can get good zippers, I will take them.

No Flap

For the same reason I want a rear mounted strap and I like the key loop, I don’t want a flap. With good zippers, the purpose of the flap is nullified.

In my furious month of research on bag fit. The Dange Dover Oslo. I had never heard of this brand. But there are lots of bag brands I have never heard of. I bought it, as it was on sale, and I used it for two weeks or so. Let’s just put it this way, perhaps the Wuben G5 won’t be the worst reviewed item of 2025. This thing is hot steaming garbage and a great example of the difference between fashion first brands and design first brands. Dange Dover is the former and Tom Bihn in the latter. It’s like with watches. Stay tuned. This bag is a design car crash, but not just a car crash with another car, it is one of those car crashes between a train and car that happens rarely but results in nothing but twisted metal and a few stray bolts. Its awful.

Amazon Links

MacBook 15”

Remarkable 2

Victorinox Bantam

Wuben G5

November 30, 2025 /Anthony Sculimbrene
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