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Our Take
If you live in a city, space is likely at a premium. Even if you've got a driveway or a garage spot, chances are you'll be parallel parking on a street at some point. An old land barge isn't a great choice, nor is a car with poor visibility.
Ensuring parkability doesn't mean sacrificing style, however. For example, the BMW X1 feels just like the larger X3 crossover, but it's got a slightly smaller footprint, so it's easier to wedge into tight gaps. Cars from Mini and Fiat are similarly designed to exude personality while fitting in the narrowest parking spaces.
If you're really into going small, minicars like the Chevy Spark, Smart ForTwo, and Scion iQ can fit nearly anywhere. The downside is that they're lacking in total cargo space, so you may have to travel by yourself if you're going out to buy furniture or bulk toilet paper.
In many cities, everything is accessible by foot, bike, or public transit. That means the only time you'll use a car will be for a longer trip outside of the city—to visit family, take a vacation, go shopping, or navigate a reverse commute for work. Keep in mind that you might want a more substantial car for these long highway trips.