My lovely fiancée just bought me the Ipad I've been drooling over for some time and I want to take it in with me to work - however my work laptop, which is a Dell, happens to be rather large about 16 1/2" diagonal.

So here is what I need to take to work everyday, luckily once I get to my cubicle I can unload almost everything and don't need to trudge anything around:

-work laptop: 16 1/2" diagonal Dell
-document binder: roughly same size as the laptop!
-ipod classic w/ headphones and charging cable
-small notebook and pen/pencil
-reading glasses
-leatherman skeletool multi-tool

and now (hopefully)
-Apple Ipad inside the Otterbox defender series case (which does add some bulk)

I hate packing a bag to overflowing so I tend to chose bags slightly bigger than the largest object.

My question - can anyone recommend a messenger bag big and thick enough to hold all these devices with the awkwardness or do I need to do the unfavorable task of switching to a backpack?

Thanks for all your help!