A very warm welcome, jutatipp, to tPF and to the Bal section. Both bags are just wonderful, but very different in their looks and use. I've had both and loved them equally. I would, possibly, see a Bayswater as a more durable and functional bag, but I use my City bags, day in and day out at work and they, too, are equally durable and functional. It's down to what floats your boat, I guess! Perhaps if you're small (as I am), you might feel more comfortable with a slightly smaller and lighter bag i.e. the City. Enjoy making your decision, since you'll certainly enjoy the bag you choose.