I use a Timbuk2 'Commute' messenger style bag. It is really more like a soft briefcase than a classic messenger bag design. It has a padded laptop compartment and lots of internal and external pockets - perfect for keys, pens, business cards, folder files, checkbook, sunglasses, electronic accessories and lots more.

I bought and use it for the reason it is like a briefcase which works for work much better than a backpack would - especially days I fly or travel/walk to meetings, etc.

It works great with zero discomfort for taking my laptop to/from work as well for a 9mi ride each way - I know somewhat longer would be OK as well. The strap is padded and I use a x-strap as well for stability.

No reliabilty or wear issues after over one year and 3500 miles on my back.

Al