The Laptop Bag

Back in February, I wrote about my search for a new laptop bag, and invited readers to contribute their thoughts and experiences with their own bags to help me make a decision.

Since then, many people have asked me what bag I decided on, asking me when I’d be posting about my decision.

This is that post.

If you’re really impatient and just want to see what I decided on, you can just jump to that section. But if you’re interested in the explanation and want to learn about my purchasing philosophy, keep reading.

Note: When I wrote my original post, I was brandishing a 13" MacBook. That system is now in use by one of the guys on my team, and I’m currently carrying a MacBook Air around with me. All of my other requirements are the same.

Taking Time

People who know me know that I often do extensive research and take my time making purchase decisions. I tend toward minimalism and generally try to reduce the number of things I own, so when I get something new, I try and make it count.

About ten years ago, a friend of mine introduced me to a great motto: A poor man can afford only the very best.

I’ve probably thought about that phrase every time I’ve made a purchase. Generally speaking, when you buy something impulsively, you’re probably going to make a bad decision. Worse, when you purchase something inexpensive (or maybe cheap is the better word), it usually doesn’t last as long as the expensive version would have. Everything breaks eventually, but cheap things tend to break sooner.

You then wind up having to replace the first thing, usually by purchasing the more expensive version (the one you should have bought in the first place). So now you’ve spent the cost of the cheap thing plus the cost of the expensive thing – more money than you would have in the first place if you’d just spent more first.

I’ve bought a number of laptop bags in the past that just didn’t cut it for one reason or another, and I didn’t want to waste money again, and I knew that lots of research would be needed. At the same time, I have a job that keeps me busy, and I’m spending pretty much all of my free time with my 8 month old son.

So the laptop bag research would happen … but it would happen slowly.

The Short List

I researched, evaluated, and tested out quite a few bags. Some of them I ruled out after online research or discussion with friends. I tried many in person, by visiting a store or by finding a friend who owned one. There were even a few I purchased – and either kept as a spare or returned.

Here’s the short list of bags I tried and liked:

  1. Booq Mamba Pack
  2. Booq Mamba Sling
  3. The STM Small Alley
  4. Incase Nylon Sling Pack
  5. Belkin Slim Backpack
  6. Timbuk2 Track Daypack
  7. The Tom Bihn Ristretto
  8. Counterfeit Mailbag

I really liked all of these bags and would have probably been happy with most of them.

As I evaluated them, I realized that I didn’t think it was fair to offer a recommendation for something if I haven’t really tested it out. In the case of a laptop bag, this doesn’t just mean taking it around with me to a coffee shop a few times, this means traveling with it … and that meant waiting for my next trip, RailsConf in May/June of 2008, to come along.

Now that I’ve had the chance to really test out and use the bag in real-life situations and while traveling, at long last, I can safety reveal my choice to Hivelogic readers.

The STM Small Alley

STM Small Alley

After many hours of online research, in-store testing, and talking with friends and colleagues, I decided on the STM Small Alley. It’s available from" Amazon": (use that link and I’ll make a couple bucks) and also from my friends at Pivotgear.

Why The STM Small Alley?

I wanted a multifunctional, minimalist shoulder-style bag that would be lightweight and easy to carry, with a padded laptop compartment, and room for a little bit of gear and a notebook. I like things that just work, do a job (or a few jobs) very well, and get out of the way.

The STM Small Alley fits this bill exactly, with no bloat, extra or unwanted features, in a no-frills, unpretentious way.

The Good

Here’s a list:

  • It’s almost weightless
  • The pockets and compartments are just the right size and in the right locations (e.g. a zipper-pocket on the back perfect for your boarding pass and ID means you don’t have to flip open the whole bag just to get certain items)
  • There are outer and separate pockets for notebooks, gear, and your laptop
  • The shoulder strap is removable
  • The flexible handle fits over most carry-on luggage handles for easy maneuvering through a concourse
  • The padded section actually worked, protecting the laptop from bumps and small drops
  • It’s well-made from durable 600d polyester ripstop fabric with PU coating for water resistance (the lining is water resistant)
  • Both the outer and inner compartments have velcro closures instead of zippers, which makes it easier to open up with one hand
  • It fits easily under the seat of an airplane
  • It doesn’t look like a laptop bag (I didn’t care about this, but it seems to be a selling point for some people)

The Bad

  • Size: this bag is just for your laptop, a notebook, and a couple of cables. You won’t be fitting your dSLR and zoom lens in here
  • You can pack it full, but you can’t really overload this bag the way you can some “expandable” bags, as it’s not elastic and doesn’t stretch
  • The zippered compartment on the flap
  • It’s not as “cool” as some of the laptop bags out there, and probably won’t guarantee street cred with your hepcat friends or get you invited to any Hollywood parties

Final STM Thoughts

I’ve been using this bag regularly for a few months now, and it’s been great. While it lacks the flexibility, versatility, and large size of my Booq Boa (the version I have is no longer made, and I’m not as fond of this newer one), it’s much less bulky, fits under seats and into other bags more easily, travels better, and carries more easily over your shoulder or in your hand.

The STM is also available in larger sizes for laptops with bigger screens.

The Runner Up

There were a number of bags that came really close to fitting my needs perfectly, but for one minor reason or another, just weren’t exactly perfect for this specific need.

Enter the Tom Bihn Ristretto Messenger.

The people at Tom Bihn are great. When ordering or researching, you interact with an actual person. The person cares about their products and your experience. The person wants you to be happy. The person’s name is Darcy, and she is incredibly cool.

Tom Bihn bags designed by a real guy who’s name is actually Tom Bihn. The bags are hand-made by people in their small Seattle factory.

This is exactly the kind of company that I like to buy things from and support. So in addition to the STM bag, I also have a Tom Bihn Ristretto. It’s a bit too lightweight for me to feel safe traveling with, but for day-to-day activities, coffee shop visits, and the like, it’s great.


I hope this post will be useful to you. In writing it, I realized that some of my requirements were so specific and some of my needs so unique, that my choice of laptop bag might be – at best – inapplicable or in the worst case, simply inconsequential.

In any case, please feel free to use the comments (below) to ask questions or discuss with me anything about the STM, the Ristretto, or the other bags I tested.

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