This bag is amazing to me. I adore pretty much everything about it.
It is on the large side, I am 5'3", 140.  Very close to national average weight/height and it hits me at mid-thigh when hanging from my shoulder. When full with only a laptop (mine is a 17", measuring 16 inches long, 10 wide.) and a binder, notepad, clipboard, agenda book, office supplies, and purse essentials like wallet (ladies sized even!), emergency makeup and chocolate, and some misc electronics (phone, cam, wires), it looks only a little clunky. If you can wear a bag without it wearing you, then this bag will hold ALL YOUR JUNK. If your stature and style is easily overpowered by a chunky purse, you might want to look at a smaller bag.

Fully packed to BUCKET status with [PC, camera, charger, 4 semi-full Binders, textbook, clipboard, notepad, agenda book, emergency reading book sized book, wallet, makeup, TI-84 calculator, glasses and sunglasses, meds,  business card holder, AND other random things that I have thrown in. ]  It will look like you are lugging around some luggage.

Let me note that my laptop is too big for most laptop bags to close on, and this is no exception, but it is 16" tall and while the Velcro flap will never be able to close the over top of the laptop pouch, my laptop fits in the bag and that is all I can ask for. I just tuck in the flap and use the pouch as an open pocket. Inside, there is one larger medium pocket with a zipper, two smaller fat pockets, two flatter pockets on the outside of one of the smaller pockets, and two pen/pencil pockets that hold 2-3 pens and pencils each.

Outside are two pockets, both with leather externals. The rear pocket is not really a pocket (to go over luggage handle) but I use it like one, though have to keep an eye on the zipper on the bottom to not spill my items. For some weird reason, the back of this pocket is liner material (though not visible at all from the outside. The front pocket unzips and opens up like an accordion file, which makes it easier to root around in. It has two flat pockets in the back of the pocket that hold a wallet or glasses etc.

Love the tacks in the corners and durable feel, and the little leather tassel zipper pull.
Experiencing some minor discoloration and forecasting that the weakest and first point to break on the back will be right where the strap is attached, and much sooner than the life of the rest of the bag is up at that.  In general, I still just love the bag. Looks so professional and goes with everything.