I'm a bag junkie. So many, and still have gaps in requirements.
Bought the LowePro Photo Sport 200 AW (orange) for trekking Inca Trail, but it was too small for a 5DmII with grip. Otherwise, perfect camera bag for that kind of trip. Wouldn't fit a 70-200 f2.8, though. And thank gods because even without carrying that beast, the bag got heavier and heavier every day.
Bought a Jill-E Jack Messenger bag years ago, and only used it to store things until couple weekends ago. Completely inadequate strap that I had to double up with a padded Canon camera strap. Who tested this thing and what equipment did they put in it? I was carrying 5DmII with grip, 24-70, 16-25, 580EX, 15" MacBook Pro + power, and various small accessories. That should be a typical kit for a bag of that size, but if that bag had to be carried further than from the car to the door of a building, the strap would carve a nice trench in your shoulder. And the carrying handle on the cover is useless for actually carrying the bag with any gear in it. Empty, fine. But with weight, really awkward. Do I continue to use as a really expensive storage container?
OTOH, the Jill-E Jack Large Rolling bag has been very useful and stylish to boot. Jill-e’s handle designs need more thinking through, however; mostly they flop unattractively, you can’t tuck them away, and they’re not really that useful for their intended purposes. Bad on both form and function. Same goes for a lot of their women’s line.
Crumpler’s 7 Million Dollar Bag is enormously useful for carrying a lot of gear. Except for a laptop. I suppose that’s why there’s an 8 Million and Brazillion Dollar model now. But if I’m going to carry that much weight, it might as well be a back pack.
Loved my LowePro Slingshot when I first got it, but walking more than 2hours with it (5DmII with two pro lenses) starts to get unpleasant. Being able to switch shoulders would be ideal. For that reason, I don’t often use this bag now. Carries a surprising amount of stuff, though.
One of the first bags I bought was a Billingham Hadley and I loved it for my film cameras. Now, I find it’s not deep enough. Still a beautiful bag and very sturdy.
Finally (not really, but I’ll stop to let someone else have a turn), I got The Image Smith Bag Mark II Black Label Bag for my Leica gear. Frankly it’s too big for what it holds, but better that than too small. It’s barely recognisable as a camera bag, and pretty much as non-descript as a manly camera bag can look.
The next bag I buy will have to carry a 15" MBP and reasonable kit. This will likely be a backpack unless I find a shoulder bag that is comfortable (doubtable).
D: iPhone 4S, Canon 5DmII, Panasonic DMC-LX3, Fujifilm F30, Canon 30D, Nikon CoolPix 8700 | A: Leica M3, Holga 120N, Contax Tvs, Polaroid Spectra, Canon 50E, Rolleicord, Canon AE-1P
Canon lenses: 16-35L II, 24-70L, 50 1.4, 70-200 2.8L IS, 10-22