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@dan
I've got a timbuk2 messenger XL guy - it's alright.. does the job.. Upgrade the strap with one of the extra grippy wrap-around things - stops it slipping all the time.
However I have had to put a big piece of cardboard in the back to stop contents poking me in the back. And I do find myself adjusting it whilst riding.. I'm sure there are better bags out there, but to be honest I only wear it for communting, it's bloody huge (which is great as I take a change of clothes/hard drive/ diaries and other crap with me a lot) .. and I've spent 70 quid on it so I'll stick with it for a while.
If I was a courier riding all day I'd probably change to something else.. but to be honest. There are other bike related things I'd rather spend my money on.. like bikes :)