The best looking car that someone can actually afford in my opinion is the Alfa Romeo 159. Mechanically these cars are rubbish and break down regularly, but is worth it to own something that looks so damn good. Yeah, these cars are actually affordable, just not available in the US...yet.
-The car I actually own isn't particularly good looking, but it is quite rare oddly enough. I have a Volvo S80, with a V8. S80s aren't rare in and of themselves, but you find one with the V8 and it's rarer than a Ferrari 458 Italia. It wasn't expensive either, depreciation on luxury cars is horrible, so they get cheap quite quickly. It was something like $70k new, and I picked it up for $19k after it was 5 years old, ouch.