11. Smart ForTwo
Some folks in their 50s buy Smart cars just for the sheer practicality of the package, usability, and easy parking. And of course, for the idea of them being cool for driving a quirky car.
However, a gray-haired dude in a Smart car looks a bit silly. So even though the car is tremendously easy to drive and park, your midlife crisis deserves a better, more mature set of wheels.