I’ve written in the past about my love/hate relationship with messenger bags.  Well, I decided to revisit….and I must say, I’ve changed my tune.  I believe that the problem I had was the fact that I wasn’t getting the right messenger bags.  I did a little reading and found that there are messenger bags and there are professional class courier bags.

After reading and reading and reading and reading, I finally had it narrowed down to two bags.  The patagonia half mass and the medium sized timbuk2 Commute Laptop TSA-Friendly Messenger Bag.  Now, I’m a huge fan of patagonia stuff.  I have some of their jackets, down “sweaters” and shirts.  They’re a cool company that makes durable stuff, but timbuk2 is on another level when it comes to bags.  I picked mine up from Amazon so I could get the prime shipping, but they’re available directly via timbuk2 for $104.25.  I chose classic black since it looks more professional in my opinion and despite my disinclination, I need to look like a grown up sometimes.

I wanted both so that I could to a compare/contrast, but due to budget I only got a standard, off the shelf, right handed medium sized timbuk2 Commute Laptop TSA-Friendly Messenger Bag.  Now, I tend to be ambidextrous, but I certainly favor my left.  I thought this may be a challenge, but I wasn’t willing to pay extra for a custom made left handed bag. I’m fundamentally against paying more because I’m a lefty….I get the reason…I’m just lucky enough that I can deal with it.

Once I got used to the right handed nature of it, I was totally sold.  Construction of it is solid, it’s made from waterproof material and the flap has a velcro option to keep it even tighter.  The zippers are sturdy and look like they’ll keep most rain and moisture out.  This may be the best bag I have owned and let me tell you why:

 Quick release strap.  This is amazing.  It basically allows for the bag to be worn in a reasonable way across the shoulder and still easily come off and go on.  This alone makes this bag better than any messenger bag I’ve ever used or owned.  I can pack it full and wear it tight to my back and still be able to get it on and off easily, over a thick winter jacket or just a t shirt.  It’s also comfortable.  Even packed full.  That’s not something I can say about any other messenger bag I’ve used.

Unique, solid, metal  quick release clips for the main flap.  They’re easy to open one handed and hold tight.  I’m still getting used to clipping them closed one handed but I suspect it’s just a matter of time.

Lots of pockets and space.  I got the medium size and I can still get an extra shirt, a quick bite to eat, all of the cables and adapters I need, an evernote  moleskine notebook, my 15″ retina powerbook, my iPad, power bricks for both and an aluminum water bottle. And I have room to spare.  The side, under flap compartment that is accessible without opening the flaps is perfect for things like a phone or keys, too.  I use that particular pocket extensively, multiple times a day.  I don’t have to take the bag off but can still get to objects easily and know they’re stored securely.  

If I could get a set of workout clothes in it, I’d be set.  If I had it to do over again I’d probably have gotten the large, but this one is working out well.

The soft lined laptop and separate tablet compartment are perfectly placed.  The really nice value-add is that the both the laptop and  tablet compartment are accessible from “outside” the bag, without messing with the flap.  Very nice design.

Since I’ll be traveling with this bag, the “TSA Friendly” zipper will likely come in handy, but that’s not what sold me on it.  The real issue I always had traveling with a messenger bag was that it wasn’t conducive to moving quickly through the airport.  This solves that issue in two ways.

First, as mentioned above, the strap is actually comfortable and able to be tightened reasonably, keeping it from flapping and moving around much when it becomes necessary to move quickly to make a flight or if running behind.

Second, the bag has a luggage passthrough that allows for attachment to a rolling piece of luggage.  This is an ingenious addition, especially for someone like me that rarely checks bags but has a wheelie bag as a carry-on.

In addition, since this bag is really made in the tradition of a true messenger bag, it will be perfect once the weather allows me to get my bike back out. It has reflective strips and a nice place to clip safety lights, a true professional grade courier style bag.

Now let me talk about the things I don’t like.

As mentioned, I’m fairly ambidextrous but I favor my left hand.  I prefer to wear a messenger bag on the other side.  I’ve made an adjustment for this bag because, just like in far too many cases, left handed stuff is either custom, more expensive, or both.  Timbuk2 offers a lefty version but it both costs more and is custom.  I understand why, but I refuse to pay for it since I can [reluctantly] adjust.   I wish I would have gotten (or been able to try out) a medium or large lefty bag.  I’d be happy to review one if timbuk2 wanted to send it =).

Overall I love this bag even with the minor gripes above in consideration I’d give this bag a solid A.

I’d love to review the patagonia half mass 15 L bag if given the opportunity….