I've had one of these bags with me constantly for about 4 years now, though I'm on my second one. Note that the only reason I replaced the original is it needed some cleanup - I emailed Timbuk2 about it and rather than having me send in my old bag for repair, they gave me store credit for a brand new one - that's what I've been rocking for about a year now. Since there was a design change between the older version of the bag and the one I have now, I'll be reviewing the newer one.
This bag comes in sizes from XS to XL - I have the extra small size. Back when I was selling outdoors equipment there was a saying - "If you have the room, you'll fill it". Deliberately carrying a smaller bag to limit your carrying capacity forces you to consider what you carry, and pack light. That being said, while not an enormous bag I still run around with Stuff and it carries everything I need it to. Here it is, with all the stuff I usually keep in it, minus the phone I used to take the picture:
|For the record - that is a wallet, pair of sunglasses, 2 sets of headphones, bag of dog treats, 2 bike tail lights, a multi-tool, dog clicker, poop bags, tire levers, some hand lotion, chapstick, keys, gym lock, & an array of pens.|
The interior of the bag is laid out with a nice array of pockets, with spaces for a phone, a key-leash, and the flash pocket (the flat one along the back where my hand is). The flash pocket, which I hated when I first saw it, has turned out to be awesome. I use it for whatever paper I need to carry around, whether that be my car insurance or a map printed off the internet.
|This is the inside completely empty. It's waterproof enough that I've never had a problem in the rain.|
|This is it with all my stuff added back in - even the XS size swallows everything|
As for how it does on the bike - despite the popularity of Timbuk2 for general use, they stick to their bikey roots. The bag features a loop for my tail light, as far as my usage goes it's totally waterproof (don't dunk it underwater, it's not a drybag). The tails of the buckle straps are reflective. Additionally, the cam adjustment on the side means that I can wear it long in "purse" configuration, then with the click of a buckle have it riding high on my bag to cycle. Sizes S - XL also come with a "Commuter strap" - a strap that goes around your body from the bag to the main strap, which keeps the bag from moving while you're cycling. The XS doesn't come with one (mine is pirated from my mom's bag, which she uses to haul her Kindle, etc). Both of these straps are highly adjustable to go over coats and sweaters.
In 4 years of usage, I've never even had a stitch come loose one one of these bags. They're tanks - they just keep going. It gets dirty, throw it in the sink with a little bit of Dr. Bronner's or some dishsoap and scrub it. I'm thinking about changing over to a backpack, but literally the only reason is for 2 straps instead of 1. But, as messenger bags go, I love my Timbuk2, and the black color makes me feel like a ninja.
|Full of my stuff and ready to rock.|