As a usual rule, I exclude technical clothing from my day-to-day wear unless I'm, well, doing something technical. The contrapositive of this rule is that I go very technical when I'm doing technical things, to the absolute and utter exclusion of style, if necessary. Witnesseth:
The Vibram Bikilas. They are running shoes, and they are fog-gray and neon lime-green. I have been led to believe that these will help with my runner's knee, so who cares if they look goofy? Very few of us are particularly graceful while running, anyway.
I've started to see men's dress shoes with Vibram-brand soles, too, though only in niche markets and usually on wingtip boots that have nothing in common with the FiveFinger model.