I'm squarely in the roller camp mainly because I travel wearing a sport coat 90% of the time and every shoulder bag I've ever carried (duffle, brief, backpack) has majorly wrinkled even my most wrinkles resistant sport coats and suit jackets. I even remove the shoulder strap from my briefcase, though it is a very small 11.6" laptop bag containing only my Surface Pro, notebook, chargers/gadgets, and business cards/pens/etc (I never carry paper files with me, and only occasionally a few flyers)