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FIVE CLASSIC CONVERTIBLES YOU WISH YOU’D OWNED THIS SUMMER

Jerry Admin

Summer 2025 is officially over if you’re a hardcore calendar guy, but that doesn’t mean the convertible season is over.

Weather forecasts are like picking a winning racehorse—it’s mostly a guessing game despite what climate grifters tell you.

That’s why I made this list—there’s still time for convertible action so here are five classic convertibles you wish you’d owned this summer, so you’d have more time in the sun.

Jerry Sutherland

The first one is the 1951 Oldsmobile Super 88.

They came with a 303 OHV V-8 so they were higher on the power curve than your average flattie-six Ford or Plymouth. That means this vintage Oldsmobile wouldn’t be completely out of place on a modern freeway, but you’re going to want to pilot this convertible on two-lane backroads on a sunny autumn day.

The second example is the 1957 DeSoto Adventurer convertible.

Some fin car guys consider this car to be finest example of the Virgil Exner fin car era. There’s no debate this DeSoto is a classic example of the 50s jet age styling, and its optional 345 cubic inch dual quad 345-horse option would easily qualify for jet-like performance on the ground. Autumn 2025 would be road magic with one of these beauties.   

The third example is another Mopar in the form of the 1962 Imperial convertible.

This car came out at a time when manufacturers were dialing back on the space age look and building less flashy cars. Despite the pullback on rocket-age styling cues, the ‘62 Imperial still commanded attention—another great topless driver for the waning days of nice weather in 2025. You can rule the autumn roads in one of the biggest convertibles ever built—that’s a priceless experience.

The fourth example of a great late-season convertible is the 1967 Mercury S-55.

You could get a Super Marauder 428 option with the S-55, so highway speeds would not be a problem, but why would you not hit some off-the-beaten-path roads in this big Merc? Summer’s over and so is the potential for open roofs—unless it’s a sunny autumn afternoon.    

The fifth and final example is the 1975 Buick Wildcat convertible.

This car was built during the peak of the smog/bumper car era, so it came with a 350 small block or massive 455 cubic inch big block. The ’75 Buick convertible still had a classic front grille that was so massive it overruled the state-mandated safety bumpers. The ’75 Buick was more old-school than new-school,so it had that cool factor you can only get when you’re behind the wheel of a massive convertible. It’s the perfect road machine for a nice autumn day.

These cars are not practical. What convertible is?

That’s not the point the week after you say goodbye to Summer 2025 because the lesson here is not how to accept a change in season. It’s about stealing more summer days from a fall season that can head south faster than Canada Geese in October.

A big classic convertible will help you make it a spectacular journey.                    

Jerry Sutherland

By: Jerry Sutherland

Jerry Sutherland is a veteran automotive writer with a primary focus on the collector car hobby. His work has been published in many outlets and publications, including the National Post, Calgary Herald, Edmonton Journal, Ottawa Citizen, Montreal Gazette, Saskatoon StarPhoenix, Regina Leader-Post,  Vancouver Sun and The Truth About Cars. He is also a regular contributor to Auto Roundup Publications.

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