I did a Steve Jobs costume, too (why not when you have all the components?). I initially wanted to carry around and present my 1st gen iMac as part of it but goddamn that thing was heavy. And fuck him for not including a writeable disk drive on that motherfucker.
I could use a new messenger and I'm down with wild/leopard prints in small doses in theory. EG did some last year to good effect. I think it looks good with olive, black, navy, less so w gray. Those are the colors I wear most, esp in outerwear.