Messenger bags have been getting a lot of flack on Ben Brooks’ blog lately as he has made the complete switch to a Tom Bihn Smart Alec backpack. He raves about the ergonomics and pockets and even makes a case that it looks kinda cool. Maybe this set up works for him, but I’m very happy with my decidedly non-hipster plain vanilla blue and black Timbuk2 Classic Messenger.

It’s almost all one cavernous compartment which gives me maximum flexibility. It’s is perfect for any combination of books, folders, iPads, or my MacBook Air in it’s Zero Shock sleeve. I leave the sleeve unzipped so it’s easy to take the MBA in and out and if I don’t need it, the whole sleeve/MBA combo stays home. I love the simplicity of never having to remember what’s in what pocket. I’ve even used it to transport pretty big boxes– they can stick out if need be and the flap can partially cover them but be secured by the strap.

It’s super-fast to open and close since I don’t have to take it off my back or loosen any straps. I can keep my bike lock there when I’m out and about and it’s trivial to pull it out and put it back in as needed.

It’s perfect for cycling–the weight is on your hips instead of your back/shoulders and that makes for much better stability. Just make sure you use the strap that attaches to a belt loop so it doesn’t swing around unexpectedly.

The ballistic nylon show almost no wear. My bag is six years old and I’ve put it through the laundry maybe three times. And it’s not like I’ve babied it–it’s with me outdoors every day rain, shine, or even the arctic conditions of last winter in Connecticut.

The bottom line: Six years from now I’ll probably be using exactly the same bag. And it’ll still look great.