Oh the irony!
There is a law in quantum physics that states that a particle can't be located if its speed and trajectory is being measured, but its speed and trajectory can't be measured if the particle is being located. This is Heisenberg's uncertainty principle, and it's useful for understanding the hipster. Hipsters reject the mainstream and refuse to be categorized, but by defining the hipster, it places them in a category and erases their status. In physics, the best a scientist can do is to find approximations for particles, and the same goes for the hipster's car choices.
The quirkiest car in the world is probably the Spyker C8 because it follows none of the traditional rules of the modern automobile. Split side windows mean that you can only roll down the glass halfway, a lack of driver aids are reminiscent of the fixie's lack of gears, and even the CEO champions smoothness over speed, something no one would guess with the aeronautical styling. It's the ultimate token for the consummate beatnik. Besides, who else would spend $200,000 on a car no one has heard of, has little prestige, and isn't a Lamborghini or a Bentley? Pull up to the local coffee shop with this and everyone would crown you as the ultimate hipster if it wasn't for the fact that classifying someone's worth based on material objects is so mainstream.
Like the hipster, the Fiat 500 is far from the most popular thing roaming the city blocks. Its styling is naturally rebellious and calls back on an era where things were simpler (and also a lot more unsafe). The fact that it's styled after an iconic-in-the-states Italian car and is built in Mexico means that it's foreign enough to be a reject on the fringes of society. It also looks satirical, and like a fixed-gear bike, the Fiat 500 is pretty impractical for anything but the city. It barely has the room to fit two bearded people up front but it will squeeze in a few six packs of IPAs in the rear before all the cargo is gone. Hey, having less possessions means you're fighting the man by not being the typical consumer, right?
The Nissan Cube is a bit less hipster than the Fiat 500, but only slightly so. It may be from a big name automaker, but its styling does the job of making it a sarcastic car very well. Cars nowadays are slick and feature sloping lines meant to catch the eye, but the Cube uses its boxy shape to not be conformed by the arbitrary rules of society that govern the design of other cars. Instead of being sleek, the Cube catches the eye by being an eyesore, and there's plenty of space in the back for those days where large thrift shop yields are a thing. An unwritten rule of the Nissan Cube is that a wry and satirical shirt must be worn by anyone inside. You don't want to be a square in a square world, but what about being a square in a curvy world?
The number one automaker in the world for the hipster is Volkswagen. It made the original VW bus, which is the ultimate automotive symbol for counterculture. The problem is that nowadays, its big cars are SUVs and we all know that popular body styles are a big no-no for the hipster community. That's why the Volkswagen Golf Wagon is the perfect car for the fair trade coffee lover. It packs all of the utility of the Touareg or Tiguan without having a body style that says "I am a slave to all trends." The fact that it's a fairly rare car means that you won't have to run into someone else who happens to be driving it because that would be like seeing someone with the same flannel as you have.
We live in a time that offers some rare opportunities for the freethinking car buyer. GM recently dumped a few auto brands after a having a near-death experience and now there is the chance to own the ultimate badge of resistance: the new car that is no longer made. The old Saab 900 was one of the best cars for reader-wearing urbanites, but it's status as a hipster car means it is no longer a hipster car (uncertainty principal, remember?). In its place, why not grab one of the last Saabs that ever rolled off of the line? Saab even considered joining forces with Spyker at one point. For the cat owners, an Oldsmobile will do well. We already know anything old is not in vogue for the modern bro, which means its name makes it perfect for the hipster.