For consumers, it's obvious that tech needs to be socially acceptable - in fact it's an expected part of the adoption cycle. For fun (ok, I'm revealing myself), and to exercise my creativity and outside-the-box thinking, sometimes I try to come up with norm-violating, harmless, and clearly more productive technology people could adopt. (I don't mean provactive norm-violating, like something dangerous or overtly sexual, just geeky or otherwise.) Simple ones are walking around town with an umbrella hat, a headlamp, a camelback, etc.
But to the point of this discussion, for business / military I wonder how much ugliness plays a factor. If a 5% more effective fighter plane was clashing shades of horrible colors (for camo) and had a laughably ugly form, would it be used? What if the pilot mounted/dismounted in a ridiculous position, maybe upside down? Otherwise, people are dying and wars are being lost for aesthetics. What about 20% more effective? Where is the line? And what about the space program: how much extra risk is taken for dignity under current social norms?