I think what rewq has been trying to say is that he doesn't want to have to settle for a nylon briefcase that looks like something an 8th grader would carry to school. Even though a person rides a bike to work, he/she sometimes has to look like a "regular" person once he/she is there.
My Vaultz briefcase cost only $30, but it is suitable and acceptable for the type of work I do. That's because when I need to carry it into a "tech" meeting with big wigs from the town, it looks expensive and it looks rugged. A messenger bag or any of those other bicycle-specific bags look like kids gear to me.
That said, the Steco rack comes close to what I would like (and what I think rewq would like), but that's a really awkward looking carry-angle.