Back to the OP. I'd vote for a Chrome bag. I'd not had much experience of messenger bags until last month when I got a Chrome Kremlin for £75 from
Chain Reaction, though it seems they are back up to £110 now. It's a fantastic bag though, really very well made, tough (lifetime guarantee), very comfortable, and after getting caught in the worst rain I've ever seen last week I can confirm that they are completely waterproof.
Only a couple of drawbacks, 1) it doesn't have a padded back so any awkward shaped or seriously heavy objects require careful packing to prevent them sticking you in the back (which won't be a problem if it's mainly clothing you are carrying) and 2) the Kremlin is maybe just a bit too big for my needs (the Metropolis is probably more than anyone would need). In fact it's so big I comfortably got my 8 year old nephew in it with space for shopping too.