I would also recommend a Back pack. Screw the look or bending to other peoples preceptions. Next to a sissy and bar pack, for you situation it seems to be best bet.
Hell kudos to you for getting out there and riding it. There is way too many that are more concerned on looking cool than riding. Nothing wrong with being cool, but ride comes first.
All that said, do not be surprised though when we all jump on the band waggon and give you shit, but it is all in good fun.
Hell I am not the coolest looking character out there, especially when I go for a long ride or group ride and put on a full face helment in order to mount the cam to, carry a orange backpack to carry the camera, batteries, etc as well as some bare estintials, but I get some decent memories for myself and try to share with others.
There is a difference between being cool and looking like you just step out of the cast of "Wild Hogs".
No still got the stickers on, the plate right side up, carry a back pack and if I got a to wear a helment, it will be a decent one. Now if I can only get Seatmaker to get me a good seat design to go with my anticipated custom pink flame job!!!!
Beleave me just riding a Big Dog will bring up the cool factor by itself.