Every time someone mentions the Courier style I have to throw my two cents in: love it!!!
I only have one, but it's my most-used Bbag. I have turned it into a computer/work tote. I can easily fit my huge laptop, power cord, camera, files, etc. in the Courier and it isn't even close to full. I carry it every day, and despite the weight of all my equipment - not to mention throwing in and out of the car so much - it looks like new. Better, even, as the leather has worn in. Super slouchy!!
And, I can use it as an everyday bag. I love the look of an almost-empty Courier. It slouches beautifully, and really hugs you whether worn cross-body or over the shoulder.
I am only abouty 5'2" so I understand how someone might be scared away by the size of the Courier, but I think it is worth a try. There are a lot of Courier fans out there, so you should have no problem with resale if you decide that the style isn't for you.