They’re not the convertibles you’ve always imagined owning. But they are fun as hell to drive.
It’s summer. Which means it’s finally time for you to make good on that vow to stretch properly before you work out, to burn your last remaining pair of cargo shorts, and to buy an old convertible. Your problem is that you were raised on fantasies of blatting muscle cars and Bueller-esque Ferrari Daytonas, and don’t know how to find something fun, affordable, and unexpected. Especially when you’re on a budget.
A convertible is the automative equivalent of vacation style—it’s not the everyday you, it’s emboldened you. Everyday you is practical, and invests in a 401(k) because your job matches and not to do so would be like throwing away money. Convertible You wears lots of floral shirts and called in sick today because you’re hung over from last night’s concert. Or maybe Convertible You likes to wear a tux when no one’s looking. Or maybe Convertible You just wants to crank some Thin Lizzy and strafe the highways. Convertible You is a blast to hang out with. And you deserve a droptop that steers into Convertible You’s special brand of eccentricity.
For less than $10,000 you can have any one of these top-down trophies. Some of them will seem like jokes—an ’80s Buick? Some of them are poised to become hot investments. Some of them are, oxymoronically, both. Not everyone out there will get why they’re awesome. But Convertible You will.
1. 1968-1985 Fiat 124 Spider
Yeah, we’ve heard all the joke about how FIAT stands for “Fix It Again Tony.” And like all jokes, this one’s rooted in truth: out of the 170,000 124 Spiders sold in America during its nearly twenty year run, only about 8,000 are still on the road now. The good news is that those 8,000 have demonstrated a rare Darwinian ability to survive (and have probably been babied). Not only is this Fiat 124 Spider more sophisticated, lithe, and advanced in engineering than any dinky British droptop of the era, it’s far less “cute.” This car is about to pop as an investment—hey, it’s rare now!—and you’ll look even smarter selling it than you did while you drove it.
2. 1992-95 Mercedes-Benz 300CE/E320 Cabriolet
You really want a 560 SL. Every elegant gentleman does. That’s why they’re skyrocketing in price, with the pristine ones hitting $20,000—on up to wait-how-much sticker prices. This early-90s droptop is your starter-Benz substitute. Same rhino-on-wheels solidness, same same right-angle-loving styling, but it has room for four and a driving experience like a buttered shipping container gliding effortlessly down a talcum powder mountain. Nothing says classy like gliding.
3. 1985-87 Buick Riviera Convertible
In every generation, starting in the mid-60s, the Riv exemplified the moment. So, yes—this means that in the mid-80s, it was a fake wire-wheeled boulevardier for divorced suburban lawyers, available only in maroon and white, with a puckered white leather interior. It valued comfort over all else, including parkability (avoid if you live in New York) and fuel efficiency (doubly avoid if your other car is a Prius). Ryan Gosling’s character drove one in La La Land, and while he may not have been the white jazz savior no one asked for, Gosling does have a way of making something slightly trashy seem awesome. (Compare Gucci’s recent runway and his scorpion-embroidered Drive jacket for proof.)
4. 1978-82 Corvette Stingray
Technically T-tops are not convertible tops. Realistically, they’re much, much worse: heavy, mirrored glass panels that are pains to remove, leak when they’re in place, and prone to shattering just sitting in the garage. But T-tops do let you pound the roof to your yacht rock—or Lil Yachty—playlist of choice. And they’re exactly why the ‘Vette of this era is a louche rolling erection of a car; a joke you’re already in on. These late model “soft nose” models, with their wheezy engines and chintzy plastic bumpers, are, somehow, the best investment opportunities.
5. 1969-70 Mercury Cougar
First-generation Mustangs, like pictures of Paul Newman in a white t-shirt, are now equal parts iconic and cliché. The Cougar was the more luxurious—and to our eyes, better-looking—muscle car in the family. (This was back when Mercury was Ford’s rich-guy brand, and not its dearly-departed denture-set brand.) With their menacing baleen grilles, hidden headlamps, and aggressively elegant profiles, the late-60s Cougars do handsome without also doing try-hard. They’re also criminally undervalued now that the muscle car era has been fully absorbed into collectible status. Cruise now, sell high later.
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