Bringing back a dead thread...
At least here in NYC, I see a LOT of "suits" carrying either a small sling bag, OR (More common) a satchel or a GASP - laptop bag!! Yep, the ubiquitious laptop bag...

Ever seen how BIG some of those things are? Some of them are even designed for an overnight business trip!

I know that in the bag that came with the company supplied laptop, besides the charger and all the accesories, I'be stuffed a FULL SIZED commercial HT (GE MPA with short battery), a first aid kit and a BUNCH of other "stuff" in the "second pocket" and it has not even expanded the bellows - and there are 3 OTHER pockets I have not touched - and no one looks twice....