Searching for a Messenger Bag

I’m searching for a new messenger bag. My current go-to bag is a red backpack from L.L. Bean, but I need something more professional for the day job. Also, with my broken ankle I find that my backback makes me top-heavy; I need something with better weight distribution while I’m on crutches (which is for about the next four-to-six weeks).

That said, a simple business-style messenger bag with only a few pockets likely won’t do — I need something that can accommodate my 15″ laptop as well as my essential geeky gear.

My typical load out is something like this:

  • 15″ MacBook Pro
  • Kindle Paperwhite
  • A gallon ziplock bag filled with electronic dongles
  • A power cord for the MacBook Pro
  • A Moleskine notebook
  • A half-dozen pens and pencils
  • Lip balm
  • Reading glasses
  • Distance glasses
  • A deck of “Don’t Die Out there” playing cards
  • A small stack of business cards
  • A small stack of blank index cards
  • A small water bottle
  • A headlamp, for walking home from work in the dark

Depending on the day I may also throw in an iPad, a second Moleskine for RPG mapping, additional pens and markers (also for mapping), and a paperback or digest-sized book (usually an RPG rulebook).

Compartments-wise, I like having an external compartment with a zip for quick access to things like my Kindle, dongles, pens, etc. Internally, I like to have one large compartment for the laptop and then two zipped or flap-sealed compartments for my smaller gear. I don’t like open compartments on the inside because stuff sends to fall out of them if the bag gets up ended.

As for the bag’s material, I’m looking for something sturdier than a cloth bag. Leather/canvas might work, as could synthetic, but regardless I’d like it to be water resistant. I walk to work most days — including in the rain and snow — so having a bag that can withstand getting wet would be helpful.

In the past I had a messenger bag from L.L. Bean. It served me well, but it was cloth-based and didn’t hold its shape well. That caused stuff to sort of slosh around inside the bag, which made getting items out it awkward. The current generation of L.L. Bean bags looks sturdier, but it lacks any external pockets and doesn’t have much personality. I considered ThinkGeek’s Bag of Holding but it looks to be too big and unwieldy (it’s also out of stock).

Naturally, I’m not the first one to go looking for a new messenger bag. I found a few good articles talking the best options:

My budget for a bag is $50-$120. Here ae some options I’m looking at:

If you have a favorite messenger bag I’d love to hear about it. Leave a comment on this post or email me at

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A few of the items that typically find their way into my messenger bag. Credit: Ken Newquist.

1 thought on “Searching for a Messenger Bag”

  1. After much research and feedback via Twitter, I decided to get the Timbuk2 Commute Messenger bag. It’s got lots of compartments (including an easy access one on the outside of the bag), room for my lunch and a water bottle, and it’s water-proof. It arrives later this month; I’ll post my thoughts on it once I have a chance to try it out at work.

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