Thought this might provoke some thought....
When I was at Music College one of my lecturers taught us about the circle of cool (beautifully illustrated above). What if someone is sooooo uncool they actually become REALLY FU*KING COOL.
It works with loads of things cars, clothes, glasses...
example: (which I doubt most will agree with) IMO, the old fiat panda is so uncool that it is actually really fucking cool! with it cordroy dash and boxy ugly shape. If you drove a beaten up old panda, with faded red paintwork and one door that's an odd colour to the beech with a surfboard on top in the summer, windows open and some good music playing on a portable cd player with little speakers plugged in (as you have no sterreo) you would be REALLY COOL. That guy that just parked next to you in his brand new ford focus playing Jack Johnson is going to show up as a poor imitation.