I have an RTT in Sapphire w/SGH ('08). I know that there are some '07 RTTs out there, but I believe that '08 was the final year for the style.
It is a sturdy, roomy bag. It has that Brief "look," but because of the structured bottom it can carry a heavier load without looking over-taxed. You could definitely fit a laptop and accessories easily and comfortably. The handle drop is about 7-8"; it can easily fit over a coat.
I used mine as a carry-on for airline travel and love it. I think that it would be a nice alternative to a Work (roughly the same interior capacity) due to both the structure and the ease of carrying on your shoulder.