Here's a couple of photos of me with my RTT. When I travel, it's crammed full, so that gives you an idea of how well this style retains its shape.
Especially if you carry around power cords and other peripherals with your laptop, I think that the RTT is a better option for a computer bag than the Work. I love the Work as an everyday bag, but the weight of a laptop/files/etc. definitely challenges the shape.
Caveat: I am only about 5'2" without heels.
(typical trip to the airport - RTT and Courier are barely enough or all of my carry-on junk!)