The Ultimate Laptop Bag: My Quest For Perfection

While not quite a digital nomad, I do travel quite a bit for speaking engagements and personal trips. When I’m on the go, I want to be able to do anything from anywhere, more or less.

This has sent me on a multi-year hunt for the perfect laptop and gear carrier.

I’m going to share my research and results with you – feel free to chime in with your own recommendations.

My current laptop, by the way, is a Macbook Pro M2 Max 13″. Most of the solutions I describe could work for a variety of PCs and Macs. [Note: Per normal, some of the product links here are affiliate links, i.e., I get a small piece of the action if someone clicks through and makes a purchase. You can trust my comments, whether positive or negative, to be my real opinion.]

NEW! Laptop Backpack Guide

To make navigation easier, we’ve put all of our Laptop Backpack Guide info on its own page – from Roger’s favorite to luxury leather to rugged tactical, you’ll find it all here: Laptop Backpacks.

The Paradox of Choice – Alive and Well

This post is really in my “Tools” space, but I’d be remiss if I didn’t bring in some marketing psychology. A few weeks ago, I had a chance to speak with Dr. Barry Schwartz, author of the bestseller, The Paradox of Choice. (See Is Choice Still a Paradox? With Dr. Barry Schwartz.)

We talked about “maximizers” and “satisficers.” A satisficer is happy when a product is good enough. A maximizer strives to make the best possible decision, may obsess over details, and ultimately may be less happy with his decision.

Our orientation may vary depending on the product. You might be a satisficer when choosing paper towels, but a maximizer when buying a high performance sedan.

When it comes to computer carriers, I’m sure Dr. Schwartz would diagnose me as a maximizer. (This article alone would be enough to convict me!) But, if you are looking for a product recommendation, you are better off asking a maximizer than an easily-pleased satisficer. Read on…

The Paradox of Choice meets choosing a computer bag - 5 field-test reviews. Share on X

The First Conclusion

My first conclusion is that there is no single path to computer transport perfection.

The bag you need depends on where you are going, how you are traveling, what you’ll be doing at your destination, and many other factors.

I’ve got five solutions I use on a regular basis. (OK, maybe that’s a bit obsessive… but I’m doing the field testing so you don’t have to!)

Before we get to the bags…

Essential for (almost) any bag

One very useful approach that facilitates rapid switching is to put all your essential gear on one or two Grid-Its (see Staying Organized with Grid-It). Not only do these make moving gear a snap, they also prevent your accessories from clumping up in the dark bottom of a bag compartment.

I love bags with lots of nooks and crannies, but it takes a while to get used to any one bag. Until you’ve used the bag for a while, it’s likely you’ll have to root around a bit to find that elusive EU power adapter or thumb drive. A GridIt puts everything in plain view.

I won’t go anywhere without my GridIts.

With that out of the way, here are my top solutions for schlepping my computer around town and around the globe.

Roger’s Current Choice – TUMI Expandable Organizer Laptop Briefcase

After 12+ years of hard use, I had to retire my beloved Heritage laptop bag. I searched far and wide for a replacement that would last that long and keep me as well-organized. I found the Tumi Expandable Organizer. After 3+ years of getting shoved under airline seats, knocked around Ubers, and every other kind of abuse you can imagine, it still looks like new. The version I’m showing here is an updated version that has slightly different features, but I’d expect it to perform the same. The key features that attracted me were:

• Lots of pockets, inside and out (great for quick access to chargers, etc.)
• Trolley sleeve and key leash
• Removable laptop sleeve (use alone to carry your laptop and a folder or two)
• Big enough to hold tech gear, a book or two, headphones…
• Expandable if you need still more room
• TUMI quality

My version is Anthracite, a dark gray color. I think it looks a bit more elegant than black – the gray sets it apart from all the other bags out there. (Oddly, last time I looked, the gray color cost less than black. Shhh… don’t tell anyone.) I certainly could have found a cheaper laptop bag, but this one had the features, quality and brand I wanted. I’m tough on my laptop bags, and had a few wear out quickly in the past. This one should be good for the long haul.

Roger’s Heavy Duty Backup – Rolling Laptop Bag by Wenger

 

In preparation for a two-week cruise that entailed a long flight to Singapore, I decided to try another carry-on approach. I knew I’d be checking a full-size roller, and I didn’t want to take both a rolling carry-on and a separate computer bag. So, I bought the cleverly designed Wenger Potomac Rolling Laptop Bag. That exact item is no longer available, but the Wenger Patriot II is very similar. Another use case for this bag is if you have to carry heavy stuff – gear, books, etc. – that would be uncomfortable slung over your shoulder.

I did far more research on this purchase than I did when buying my last car. Finding the right combination of features was surprisingly difficult. The key features I wanted were:

• Wheels for rolling through airports.
• Room for computer, tablet, and road warrior gear.
• Room for noise-cancelling headphone case.
• Room for a few small clothing/miscellaneous items.
• Fit most overhead bins on regional jets.
• Fit under most airline seats if overhead is problematic.
• Trolley strap for attaching to my larger suitcase for easy transport to taxi or hotel.

This list sounds straightforward, but a surprising number of bags don’t meet all of these.

The trickiest requirements are those related to getting the case onboard an airplane and then storing it. Big jets are rarely a problem. The biggest problem in the U.S. comes with the regional jets flown mostly by affiliates of the major airlines. I try to avoid small jets from Embraer and the like, but sometimes that’s all that’s available. Typical rolling carry-on bags almost always have to be gate checked, which often results in a scrum on the jetway and a delay getting to one’s next flight.

Bag-within-a-bag

There’s one unique feature of the Wenger that sold me on it over other rolling laptop bags.

That feature is the pull-out “slimcase” messenger bag that forms your laptop storage compartment. You can put your laptop, a tablet, a folder or two, a power adapter, and even a GridIt of accessories in this “bag within a bag.”

That gives you two advantages. First, if you roll up to the jetway and the gate attendant absolutely refuses to let you board with the rolling bag, you slide the small one out and let them gate-check the roller.

This can be done in seconds vs. the usual chaos of trying to find and extract important items before they take your bag away. You not only have access to all your important stuff on the flight, you also prevent your expensive gear and valuable data from being turned over to sketchy baggage handlers.

The second advantage to this pull-out bag is at your destination. If you have meetings to attend, instead of showing up with a bulky rolling bag, you can take what you need in the comparatively sleek and business-like messenger bag. It’s handy for things like taking your computer and a few papers to work in a hotel lounge or coffee shop, too.

I’ve only taken a few trips trips with this bag, but so far it has worked as expected. I haven’t yet had a problem stowing it overhead, and the inside bag has been handy both on the flights and at my destination. The Potomac holds all my electronic gear, my headphones, and a few small clothing items with ease.

There are only a few things not to like.

First, it’s blocky and and the two big compartments are semi-rigid. This offers good protection for what’s inside, but limits your ability to squeeze the bag into tight spaces. Even removing the inner bag doesn’t actually let you compress it much.

Second, I find the appearance to be utilitarian. It’s well-styled, but it is clearly a ballistic nylon computer bag. Soft, flexible leather construction for both inner and outer bags would be more to my taste but would probably compromise weight, durability, and protection. Its image is more “tech support guy” than “executive.”

The third issue is the slightly deceptive “overnight” compartment closest to the handle. It looks huge from the outside, but the handle assembly takes up a good part of the space inside. The compartment is still useful, but is best for small or soft items that can fill the space on either side of the handle.

Conclusion. If you want a computer bag that rolls, this may be the best choice due to the removable messenger bag. It isn’t high fashion and it’s a bit bulky, but it gets the job done.

 

Old Reliable – Heritage Leather Computer Bag

This bag logged 400,000+ air miles and accompanied me all over the globe. I had to retire it as the leather surface began to wear out, even though it was fine structurally. Funny stories… a couple of years after I retired mine, I saw a fellow flyer boarding with the exact same bag, color and all. I told him I had used one like that for years, and his face lit up. “It’s my third one, I love it!” he exclaimed. A year after that, I was contacted by someone who found this post and was desperate to find a new Heritage bag to replace his old one. I assumed it was a futile quest, but I searched and found a lightly used one on eBay or Poshmark. I briefly considered buying it myself, but I already had my TUMI. I sent him a link, and later got a nice thank you – he had bought it and it was great. So, if you can find a used one of these – snap it up!

Unfortunately, the Heritage brand seems to have disappeared, but this model is fairly close: Claire Chase Executive Computer Briefcase

PC Treasures PocketPro Padfolio Portfolio Case

This little carrier gets used more frequently than any other bag in my collection, despite its rather severe limitations.

It gets used a lot (almost daily) because it’s my way of taking my computer to the coffee shop for an hour or two of “co-working.” My battery lasts far longer than that, so there’s no need to carry a power adapter. I forgo a mouse, too, and rely on the trackpad.

I love certain aspects of this case and hate others.

On the plus side, it provides great protection for my Mac. The sleeve is very well padded, the exterior is fairly stiff, and a zipper seals the unit inside. I’m not going to test it, but I’m pretty sure my Mac would survive a drop onto a concrete sidewalk inside this case.

It’s also sleek and reasonably good-looking. The exposed red liner on one side is a bit superfluous, but I wouldn’t be embarrassed to show up at a board meeting with this case. I expect it would work well with similarly sized Ultrabook PCs and large tablets.

On the minus side…

First, there’s no handle, shoulder strap, or any other way to hang onto it. You can hold it in your hand or tuck it awkwardly under your arm. Juggling this case, a cup of hot coffee, and your phone or wallet, is possible but decidedly risky.

The lack of any handle or strap also makes it a less than ideal choice for long carries. It’s fine for car to office or office to conference room, but on a twelve block hike carrying it might prove to be a bit much.

The other problem with this case is its utter lack of storage, despite being about two inches thick. The outside pocket (where the red is visible) is very tight. You can insert a thin manila file folder, but it will stick out. That looks cheesy and the file will get dog-eared.

There’s a small zippered pocket inside that might hold, say, a few business cards or a folded note.

Two small, very tight pockets could hold a few more business cards, or, with some pressure, a passport. A wider zippered compartment could hold a few sheets of paper if you could shove them in without crushing them.

The operative word for all of the supposed “storage” is tight. These compartments seem to be more for show than for effective use.

Most significantly, there’s no secure place for a file folder or two, logical accessories for, say, a lunch meeting. The only option is to stick a folder in the middle and bring the halves of the padfolio together.

If you do this, the folder fits nicely and doesn’t stick out. The catch is that you are relying on friction to keep everything in place. Chances are your important contract won’t slide out the open sides, but it’s a bit unsettling to put a folder in with no real barrier to the outside. Using a zipper to attach the halves would have provided secure storage for files, loose papers, etc.

The last oddity relates to the small zippered compartment. Not only is it so small and tight as to be useless, but the zipper pull tends to gouge anything it touches, like the legal pad or any papers you stick in the middle.

Conclusion. This is an attractive solution for protecting your laptop and carrying pen and paper. Use it for nearby meetings, a jaunt to the coffee shop, or any time you want your laptop with you for a short time. Lack of handles and near-zero storage make it impractical for anything else.

Photos, specs, and buying info: PC Treasures PocketPro Padfolio Portfolio Case

 

Latico Men’s Park Avenue Laptop Briefcase

Here’s the newest addition to my computer carrier stable. It’s a compact messenger-style bag with carrying handles and a shoulder strap.

My current use for this bag is nearby travel, longer meetings, etc. where I need more capacity than the padfolio. With this bag, I can pack an array of files, my Mac power supply, and even a GridIt or two.

This bag is a bit like my reliable Heritage bag, but with one less big compartment and a much sleeker profile. It’s about a third of the thickness of the Heritage bag. And, the dark brown color is more to my liking.

One trend I’ve seen in my own technology use is that the gear I’m carrying is shrinking. In some cases, I’m able to eliminate items. The last time I used my Ethernet cable was a couple of years ago – do I still need it?

Similarly, if I have my iPad, do I really need the space to carry paper books on trips?

I see this bag as the future for my business travel. As I continue to slim down my essential gear, I’m quite certain I could use this bag to replace the much bulkier Heritage bag.

The one item that really overloads this bag is the case holding my Bose QC-15 headphones. I’ve found the superb noise attenuation they provide essential for long flights. One solution I’ve used occasionally with my Heritage bag is to attach the headphone case to one of the bag’s carry handles with a carabiner. It’s not a great solution, but it works for getting on and off planes and keeping the headphones handy.

A better solution, perhaps, would be to switch to Bose earbuds. Reviews suggest they aren’t quite as good at sealing out cabin noise, but they would offer an enormous size advantage over my QC-15s.

Sometime soon I’ll take this bag on a business trip and report on my findings.

Conclusion. The Latico Laptop Briefcase is attractive and roomy enough to hold technology essentials – laptop and tablet, power supplies, and a modest amount of other gear. It’s the future for my business travel. (I hope!)

Photos, specs, and buying info: Latico Park Avenue Laptop Briefcase. (Unavailable, but the Time Resistance Leather Briefcase is similar)

Quest for the perfect laptop bag - 5 field-test reviews. Share on X

See also: Laptop Backpack Guide

Your Turn – What’s Your Top Choice for Tech Travel?

I know many of my readers are constantly traveling, too. Please share the results of your experience in a comment!