I'm 6'-3", with 'big and tall store' shoulders, long arms, and a big chest. My Chrome Citizen fits really well if it's about half full, maybe 8-10" of 'stuff' in the bag. It hugs my body, like a comfy envelope.
If I try to put lots of big stuff inside - say, a bike helmet, pair of shoes, and a change of clothes - it starts getting too bulky and becomes much less comfortable, mostly because the stabilizing strap starts cutting into my underarm, and the shoulder strap starts getting too close to my neck.
Which shoulder? Dunno, I use the standard 'left shoulder' one and it's fine. It feels more natural to fish around in the bag with my right arm.
I'm probably 'scaled' more to a Metropolis. I've been trying to get one, but Chrome's stock is really low after Interbike, and I have no idea when they'll have the colors I want back in stock.