What IS your Laptop Bag?

**NOTE: The links in this article have been fixed. -M

I have been in a bit of a ‘writing rut’ of late and I am sorry for that.  This week I sat down and decided to write something… anything.  While I am working on a few technical issues these days none of them are very inspirational, so to break my rut I decided to write a piece about something completely different! -M

Forrest Gump: Those must be comfortable shoes, I bet you could walk all day in shoes like those and not feel a thing.

Nurse: My feet hurt.

Forrest Gump: My momma always said you can tell a lot about a person by their shoes, where they go, where they’ve been. I’ve worn lots of shoes, I bet if I think about it real hard I can remember my first pair of shoes.

In this day and age of mobility it is easy to imagine an alternate version of the opening scene of the classic movie:

Forrest: That looks like a comfortable laptop bag.  I bet you could carry that laptop bag all day and not feel a thing.

Nurse: My back hurts.

Forrest: My momma said you could tell a lot about a person by their laptop bag… where they go, where they work.  I’ve carried a lot of laptop bags.  I bet if I think about it real hard I can remember my first laptop bag…

I am spoiled… I admit it.  I have indeed carried a lot of laptop bags, and to the best of my recollection I have never paid for one.  The first one I had was a leather Targus bag that came with my very first laptop (a Gateway 486 model that I bought second-hand) and was completely mismatched to my circumstances… it must have looked amusing to people to see me traveling on the train with an M-16 assault rifle and a leather laptop bag – back in the days when most people did not have laptops!

My second foray into mobile computing was with a Toshiba Satellite A70.  It was (at the time) blindingly fast, with a Pentium 4 processor.  It was also purchased used, and fittingly was going to go right into the old Targus bag when a friend stepped in and gave to me a TechNet branded laptop bag that he had won at an event.  I was thrilled – at the time I thought there was a cool factor associated with carrying the Microsoft branded bag!  I was so proud of it, not realizing it would be one in a long string of bags…

That was in 2005, and in the eight years since I have likely gone through three dozen bags.  Some of them were event-branded (WPC 2012 & six consecutive TechEd North Americas), others were product-branded (you can imagine the number of Windows bags I have gone through, including Windows Server, Windows Vista, Windows 7, Windows 8, SBS, Microsoft Office, and more).  A few of them were branded by different teams or divisions within Microsoft (Microsoft Learning, System Center, MSN, MSDN, TechNet) and a few were branded by other companies (HP and Dell have given me bags, but one of my current favorites is Veeam).

The Microsoft MVP program has contributed more than a few to the collection, including a messenger bag I rather liked (but whose shape was not entirely compatible with the laptops I owned), a nylon briefcase-type bag that I think my wife is currently using, and most recently a backpack branded Microsoft as well as the MVP logo, this time in red (instead of the usual blue) and a Canadian maple leaf. 

I have, as a STEP presenter as well as a Virtual Technology Evangelist, been given bags to give away… they are always a popular giveaway item, and the branding is almost as important as the design/style.

With all of the discussion about branding one might think that all I care about is that the bags are free or cool.  Nothing could be further from the truth.  Functionality and comfort are frankly the only things that really matter to me in a laptop bag… and while it may sound strange, I have narrowed my ‘everyday use bags’ down to four, depending on where I am going and for what.  The winners are:

1) Ogio Module (branded Windows 8)

I am not going to say that my Microsoft Surface Pro saved my back, but it really did go a long way to my rethinking my load, down to the bag that I carried.  The messenger bag that one of the product teams gave me a few months ago has room for two Surfaces (the Pro and the RT) plus a ring binder (I still take notes by hand, and having the notebook with me ensures that I can continue to do so even when told to turn off my devices.  In addition I carry a single power charger for the two devices (one might run out of juice, but never two at a time), a Microsoft Wedge Touch Mouse (not my favorite mouse, but compact and Bluetooth), a stylus, my video dongles, a micro-USB cable, and my a-Jays Four earphones.  That’s it.  The fact that the bag doesn’t have room for anything else ensures that this slung messenger bag will never weigh more than 5lbs… a relief when I am on the go!

I have, by the way, gotten more than a few comments about this bag.  Whatever its advantages may be, there is one downside… it looks like a murse!  I have had to explain to numerous people that it was actually a messenger bag, and I was not trying to make any sort of metrosexual statement with it… not that there’s anything wrong with that 😉

2) Brenthaven Prostyle Lite Expandable SC (branded Microsoft Learning)

Unlike many of the laptop bags that I have gone through, this is a subtler, classical briefcase-type bag, rather than the larger backpacks that are very popular these days.  I got it as a present from Microsoft Learning at WPC in 2012, and love it for the subtlety of it (the branding is black on black, so hardly noticeable), as well as the size – while it easily fits my 14” X1 Carbon laptop, its size and design are not conducive to carrying much more than the necessities.  It has space for a mouse (currently a Microsoft Explorer Touch Mouse), the charger cable, and not much else (unless I want/need to expand it by unzipping… which I seldom do).

When I am close to home and need the power of the X1 Carbon over the compactness of my Surface Pro I will carry this bag, although it is not uncommon for me to take both with me… the two combined still weigh less than my old laptop bags, and I can distribute the weight across both shoulders.

3) Wenger Swiss Army Scan Smart Backpack (co-branded Windows Server 2012 and Veeam)

The backpack is bigger than my previous two choices, and when I am traveling this can be important… when getting onto an airplane I may not need my external hard drives and other sensitive equipment on board, but at the same time I will never again trust an airline to check my fragile equipment (thanks to a mishap in Saskatoon) so I make sure that anything delicate is in my carry-on.

The laptops that I carry with me may not change, but when I travel I carry a lot of things that I wouldn’t need at the office… a docking station, speaker and cables to connect to watch movies in the hotel (as well as an external DVD player), cameras, and a bunch of other stuff.  I also put a couple of non-IT related things in the bag – namely my Black Belt and Taekwondo uniform top (I can easily buy a pair of track pants, but replacing the top and belt is impossible).

Depending on the length of my stay in one place, once I get to the hotel I usually unpack the backpack and continue on with the messenger bag or briefcase (which I will have packed into my suitcase).  One advantage of this system is that by emptying the bag every time I can reevaluate the importance of the odds and ends in the bag, allowing me to shed unwanted weight.

4) Ogio Terminal (branded Windows & Microsoft MVP)

This really is a ‘last but not least.’  In truth it is (by far) the largest of the four, and is only used for one specific purpose: My traveling datacenter.  When I am teaching my Private Cloud class (or one of the many IT Camps that I deliver for Microsoft Canada) I need to carry a pair of 15” laptops with me, plus the chargers and other cables needed for the deliveries.  Each laptop weighs about 9lbs before the massive chargers are taken into account, and while checking these systems is unconceivable, so is any bag that is not on wheels.

The fortunate bit is that I usually have enough space in this bag to place all of the extras that I would usually need the backpack for, so I will often travel with this bag and my Ogio Module bag.  Because it is designed to fly it fits into the overhead space of most airplanes, and for the exceptions I am glad to gate-check it because I will see it being loaded on and then off-loaded from the baggage area.


My laptop bags may all be freebies (as was my golf bag and a few others lying around) but when it comes to actual luggage I am a lot pickier… although this is a reasonably new phenomenon.

I remember one of my suitcases falling apart after a long tour.  My wife was in the US visiting family and I asked her to pick up a new suitcase for me while she was down there.  When she told me what she had spent I was floored… until I realized that there really are better suitcases.  What she came back with were two Briggs and Riley Baseline suitcases.  My friend and colleague Jay Ferron had bragged about his before, how they were not quite indestructible but it didn’t matter because the company would fix or replace any suitcase (even if it was damaged by an airline) for free. 

Since then I have decided for myself that I will never go back to cheap luggage.  The quality is obvious, and for the number of miles I travel in a year (over 100,000) whether by plane, train, automobile, or boat, I do not want to have to worry about any luggage failures.  After nearly four years both cases have a couple of dings, and before my next big trip I will likely have to send them in… but not to worry, I know it won’t cost me anything to have them restored to nearly-new condition.


The bags one carries says a lot about a person.  When I tweeted that I was working on this article a colleague commented that the contents say more… but unless the person is willing to let you rifle through the contents of his bag, it is the bag itself that will give you the impression.  What impression you want to give is up to you. 

When choosing a bag you should remember that it will be a part of you – and your appearance – for years to come.  Do you want to look practical, professional, stylish?  Do you want to look ergonomical or economical?  Do you have to carry a heavier load… remember that even if you are strong and in good shape this may have long-term effects on your back and posture.  However if your bag is too small it might require you to replace it.

Protection – don’t leave home without it!

Fashion versus practicality is an interesting conundrum for many, but as I am seldom seen as a fashionable guy I don’t worry about colours or style, only look and feel (and practicality).  Although I would never tell someone to buy a $90 brand name shirt over a $40 no-name shirt, I will say that there are cheap laptop bags that feel cheap, and end up costing you in the end because you have to replace it. 

It is also important that the bag you select protects your gear.  Several years ago I had a customer who bought his daughter a $3000 laptop and a $15 laptop bag.  She asked me to take it to my office to clean it out (it was severely infected) so she packed it all up in her bag and gave it to me.  As I walked out of their office to my car the carrying strap snapped, the bag fell to the ground, and aside from a few dents on the screen I suspected the hard drive might have been damaged; unfortunately we couldn’t verify this because the 17” screen was smashed into little pieces.  It cost $1500 to fix, and would never have happened with a decent bag.


When I got my first laptop in 1996 there wasn’t the same variety in laptop bags that you have today.  They were black or grey, and essentially came in one general size.  Today with laptops outnumbering desktop PCs (and tablets set to overtake laptops in the not-so-distant future) there is a bag for everyone – colour, design, style, whatever you want.  However when you go shopping for your bag remember that it will be a part of you whenever you take your system with you.  Most of us do not change our laptop bag every time we change our clothes, so buying a bag because ‘it goes well with that outfit’ may make sense right now, but unless you can afford (and want!) a bag to match every outfit then practicality should win the day.

You might buy something that matches your personality… there are designer bags of course.  I would worry less about a bag going out of style in a year or two because that may be the lifespan of the bag anyways.  Buy something that you like, that holds (and protects) your gear, and that you won’t be uncomfortable carrying wherever you go.  If you opt for wheels remember that your laptop doesn’t like all of the jarring vibrations of city streets so you might buy an extra protective sleeve to double-up.

In short just make sure it works for you… good laptop bags are not cheap and should not be looked upon as disposable.  Give it the same consideration you would a pair of every day shoes… try it out, make sure it fits and is comfortable, and make sure it is what you like.  Nobody else has to carry it!


9 responses to “What IS your Laptop Bag?”

  1. Good article!
    In life, we collect a lot of baggage, it might as well be practical.



  3. Sebastien Dupuis Avatar
    Sebastien Dupuis

    On my side, my last 2 bags have been Everki backpacks and they are well worth their price. These things are made to last… a long time. A compartment for the laptop and another for the tablet. Well thought out product and built to last a long time. Worthe checking these out for sure!

    1. I will check them out Sebastien! As I said there is no one right answer or one right bag… I love hearing about alternatives!

  4. Which of these laptop bags would you purchase, if you had to make a purchase? Would you purchase the pricey Ogio bag?

    I always enjoy reading your posts. They are full of a lot of good information plus they also include a lot of your personal experiences. This is part of what makes your writing so very interesting and a must read.

    1. That is a great question Linda… it would depend on what I was planning to use it for. If I could only buy ONE bag then I would probably go for a good Ogio or Swiss Gear backpack.

  5. Mitch, I have a Booq Courier 10 and it looks like a murse too. But it fits my Dell Latitude 10 and a Logitech BT keyboard or even my Samsung Chromebook — and not much else. That means I don’t carry a bunch of other stuff.

    1. Doesn’t it make life easier when your bag makes you become more efficient? 🙂

  6. […] actually start with what the bag actually is… In July of 2013 I wrote and article called ‘What IS your Laptop Bag?’  I am no longer in the business of shilling for other companies, so rather than use the […]

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