DEFINITELY "a casual guy who just throw your **** in the bag and go?"
I'm low profile, carrying a black nylon backpack now but it's just too large, I end up carrying too much as a result.
I hate to say purse but I need something to empty my heavy pockets into along with room for a laptops, paper notebook etc.
It's hard to find that 'manly/cool' everyday bag...
It depends heavily on your taste... I also have a profile (CEO, carry a lot of stuff etc...) like you, but I'm very casual and to be honest I'm not to obsessed with the looks of my bag (I'm not a fashion model). My bag had to be very practical and functional and with a 17" MBP you don't have a lot of choice to be honest... In the end I went with the Targus TCG200 messenger bag Link
With the Targus I got a lot space for a very acceptable price and it not looks too bad, so I went with it... And I like it very much. For short (1-3 days) business trips I'm currently looking at a laptop trolley where I can carry all the stuff I have in the Targus messenger bag plus some extra papers and files and enough clothes for a short trip...
To be honest, there is enough stuff for you out there, so just buy what you like and don't forget about practicality and safety for your electronics (cushioned sleeves...)