I'm also trying to decide on a new laptop bag that is office-friendly but could also support a 1-2 night trip on its own. It sounds like the Pilot would work well with a 14" laptop and couple changes of clothes, but no extra shoes. While I'm attracted to the extra space of the Western Flyer, I really like the looks of the Pilot much better (and honestly, if I need the extra space, I'm perfectly fine just taking my B&R cabin bag or roller).

One curiosity I'm hoping someone can answer - I see above people have fit their QC35 cases in the Pilot, but are you doing that in the main compartment or one of the two front compartments? I have the Sony MDR1000X, but I believe the Sony case is roughly the same size as the QC35.