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I understand Crumpler's origins lie in camera bagging kit - but I've no experience of this.
As far as their courier / messenger bags are concerned, I think they turf out good quality and good looking kit. Chrome would probably be another contender, but while their products are tough as old boots (my everyday choice of bag) they don't do it for me on the aesthetics front. And they have floppy seat-belt strappage.....
I have some Crumpler camera bits and they're not much cop IMO. Timbuk2 were decent early on but have been poor for ages. I bought one in SF around 2008 - the clips snapped after weeks. The blue one above is late '90s... it's been The Bag That Will Not Die. Looks rough as hell and leaks now, though.