Driving a Pinto like it’s a Porsche

Dear Hipster:

I have been contemplating a new car for a while now. Try as I might, I can’t find one that suits me. For starters, it is getting hard to find a ride with any character. As if that weren’t bad enough, it turns out the sticker shock I’m getting whenever I contemplate buying a new car is totally justified, because cars are becoming proportionally more expensive every year! After careful reflection, my alternative choice has become clear: I must purchase a cool, vintage vehicle as a means of both saving money and cruising in style. I would like to narrow down my choices. I am no gearhead or boy racer. I just want something rad. I realize you have fielded a few questions that boiled down to digressions on station wagons as the pinnacle of automotive coolness, but surely there must be more to it than that? If I want to, as Eminem puts it, pull up to the club in a Pinto like it’s a Porsche. What are some colorful options?

— Marc

Sure, you could buy a 2001 Kia Sephia for less than the cost of a set of tires on most new cars, and it would get you from here to there, at least for a while. But you said “cool,” so pick something from any of these categories.

Old School SUVs Everything about a contemporary, egg-shaped “SUV” makes you want to yawn; and everything about, say, a vintage Jeep Grand Wagoneer makes you want to recreate your favorite 1970s or '80s road movie. I mean, who really needs to go more than 55 mph, anyway?

Vintage Luxury Cars Did you know you can buy a 30-year-old Rolls Royce for a (relative) pittance if you shop around a little? The luxury barges of yesteryear may have ceased to set the standard for motoring in sumptuous opulence, but that doesn’t stop you from hoarding Grey Poupon as you laugh at the peons in their CR-Vs. Be wary here. Buying a used Rolls Royce is one thing. Keeping it running is another.

Old, Weird European Cars Driving any European car older than, say, 1990 gets you automatically admitted into a society of weirdly obsessive fetishists. People who drive old BMWs speak in a perplexing argot of hexadecimal callsigns (“I S54 swapped my E30, and I’ve got an M40 for the 2002”), and the cult of old Volvos shrouds its precepts behind a veil of Masonic secrecy. These worlds of arcane knowledge about subjects most ordinary people have long since stopped caring about are all but irresistible to most hipsters.

VW Vans. Formerly a cheap, effective means of conveying filthy hippies between their various states of unemployment; now the ultimate mark of bohemian joie de vivre, and with the rising price tags to prove it.

Crappy American Not-Quite-Muscle Cars Boomers have long since snatched up all the cool, old muscle cars, driving the price of anything worthy of inclusion in Dazed and Confused into the ionosphere. Not so for 6-cylinder Chevy Nova sedans, Ford Pintos, and Dodge Darts. Be like Matt Damon at the end of Good Will Hunting.

Radwood-Worthy '80s and '90s Whips In case you haven’t heard of it, Radwood is a hipster gathering that celebrates the radness of the '80s and '90s. The Radwood style encompasses everything from a Lamborghini Countache to a Chevy Beretta. If it’s got colorways ripped straight out of PeeWee Herman’s television living room, you’re good to go.