No one but actual, honest-to-God bicycle messengers had the authority to wield a Timbuk2 messenger bag. If you were an iron-assed hard case living life on a bike, you’d probably earned the right; though you might still have found yourself the target of diluted messenger disgust.
That was the pervading vibe 15 years ago when I bought my first Timbuk2 bag, a Bolo (back then, each size had a name; the Bolo was the large version). Make no mistake, these were Messenger Bags: simple, voluminous, virtually indestructible black holes, able to swallow an inordinate amount of awkwardly dimensioned deliverables, specially stabilized for use on the bike exclusively. The only grudging nods to civility were a couple of pockets sown onto the outside of the bag and an optional padded shoulder strap.
And apart from a few minor changes, it’s stayed that way. Like the coelacanth, the Classic Messenger has remained a living fossil, unchanged, while other Timbuk2 species have evolved and developed around it. Until now.