Underwhelmed: First Look at a Custom Timbuk2 Classic Messenger Bag

Back when I worked at the bigger-chain bike shop here in MN, I bought a stock Timbuk2 Classic messenger bag. That was probably around 2005 or 2006. That bag has seen a LOT of use — both on and off the bike — and after nearly 10 years, it was ready to be replaced. Sometime during that decade, I also received, as schwag, another Messenger similar to the one shown above (with a Paypal logo stitched into it) — and the laptop accommodations in it were fantastic. (It wasn’t big enough to accommodate all my crap for actually commuting, however.) After a decade using that initial plain-black Messenger, I was pretty well sold on a new custom Timbuk2, because if the previous edition held up for a decade, and they offer a lifetime warranty on the new bag, what could go wrong? Well. Plenty.

It used to be that a custom Timbuk2 gave you a shit-ton of options for building out a new bag and the end result was something truly unique. Now, it seems that it’s more of a question of color scheme and whether or not you want a laptop sleeve inside it. I didn’t really mind that, though as I knew what I wanted (basically a Classic with more reflective surfaces, a solid laptop sleeve that would keep my electronics safe, and still have the room for my shoes, clothes and a towel so that I didn’t have to store stuff at the office. Obviously, that meant an XL classic. After talking about the purchase with the wife, I sat down and hashed out a design that I was pretty stoked about — crater laptop sleeve, reflective trim and center panel, and a new shoulder strap pad (the old one was disintegrating), and burned a $184 hole in the magic money card.1

The wait was insufferable. Okay, I was insufferable. The wait was interminable. It got here this morning. I unwrapped it, started looking at it and was…underwhelmed. Extremely so. Whereas my old Classic was this durable monstrosity, the new custom Timbuk2 seems as if it is built to fail you in some way. The crater laptop sleeve isn’t something that I’d trust my Macbook Pro to — it’ll protect the laptop from the contents of the bag, but when you hit the pavement, I have a feeling it’ll be just about as effective as a sheet of paper in sparing your computer any sort of damage. The strap on the newer bags is no longer the super-durable heavy Cordura strap that would have been at-home on any of my milspec gear when I was in the Army. The new strap is the same width and is noticeably more flexible and lightweight than the strap on the older Messengers. The padding on the new shoulder pad is also ridiculously thinner than the older version. I can’t imagine using the new bag on my commute2, given the duration and the amount of shit I had to haul.

I’m so very tempted to give this a preemptive two-star rating, but given that it’s got a lifetime warranty and I haven’t put it through it’s paces for anything long-duration yet, I’m willing to call three stars. It’s obvious that Timbuk2 has become more of a “style” brand than a “functionality” brand, based on my examination of the product.

Next time, I’ll look at bags in-person before selecting something — the fact that a custom set of colors and (very limited) features can be selected will have to be a non-consideration.


Verdict: tentative 3-star review, pending long-term durability check.

Review Date
Reviewed Item
Custom Timbuk2 Classic Messenger bag
Author Rating

2 thoughts on “Underwhelmed: First Look at a Custom Timbuk2 Classic Messenger Bag”

  1. Is that a photo of the bag you reviewed? I love my classic that I bought I dunno I think around 2002-ish (which is now in Tokyo, living with my daughter). I love that bag so much I just ordered a barely-used classic from ebay and it was only $50–LESS than what I paid back in the day!

    • Unfortunately, no, it’s not the same bag as I reviewed. That’s a stock image of a Timbuk2 bag. The bag, cosmetically speaking, looks fairly similar. If I’d had my choice, I would have gotten a bag more similar to the 10-year old classics. Next time, I think I may try a Chrome.

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