The New York Times had an odd post recently in which it responded to men who were having trouble carrying their iPad around town in a masculine fashion. According to the article in its Fashion & Style section, some men have even eschewed taking their iPad in public just because there's a lack of suitably macho bags. Scott Stein at CNET even rated iPad bags in terms of their "humiliation index."
I've used a laptop for many, many years and I'll admit this isn't a problem that's ever occurred to me. Any doubts or questions about my bag are instantly dissipated when I bust out awesome technology like the iPad. I guess I could see a bit of embarrassment if you're wearing a funky fanny pack or something, but there are tons of great looking bags for the iPad. Just check out the Booq Boa push bag, for example
If you really have trouble with establishing your masculinity via your gadget bag, let me suggest using a Sharpie to draw some skulls on it or maybe add some spikes.