It seems as though just about every car manufacturer has at some point, or another, developed a convertible. With such a wide variety of convertibles to choose from, we thought it would be worth putting together a list of some of our favorites that fit the dapper dandy or prep looking for a fun summer car that showcases their lifestyle with a hint of sprezzatura and panache.
Forget the supercars, the soccer-mom Sebring and the convertibles you see by the hundreds on any road that’s not covered in rain or snow. We wanted to focus on cars that are well respected but lack the popularity of some of the more modern convertibles on the road today.
We don’t expect you to agree with our choices. You may think some of the cars are ugly, too feminine or perhaps just not your style, but I’m sure you’ll post a really positive response in the comments section anyway.
When Lotus introduced the Elan in 1962, it became an instant hit with the European gentleman. Produced until 1973, before being reintroduced as the ‘Evante’ in the 1980s, the Elan has long been regarded as one of the finest convertibles of its time. A more practical replacement of the Lotus Elite, it was created as a way to mitigate the expensive costs of producing the Elite and its unfortunate reliability issues making it a maintenance nightmare. The Elan, however, was just as elegant but offered a far more reliable ride at a lesser cost. If you’re looking for a vintage 2-seater with compact, European styling, the Lotus Elan might be the best pick for you.
Austin Healey 3000 MKIII
When I turn 50, this is the car I want. Well, this or a Jaguar XK-140 Roadster, which you can read about below.
The larger version of the notoriously compact British sports car, the Mark 3 was introduced in 1963 as a replacement for the Healey 3000 MKII and MKI. It remained in production until 1967 and offered roughly the same options as its predecessors with the exception of being downgraded to a standard vinyl with leather being considered an upgrade. Today, the MKIII is a well-regarded collectors car, perfect for summer drives along the coast. Just be sure to pay into an auto-program like AAA because they’re not exactly known for being the most reliable cars.
1957 Mercedes-Benz 300 SL Roadster
It doesn’t get much cooler than the 300SL. A bonafide Bond-style car, it was initially introduced as a race car before being moved into production in 1954. Less than 2000 roadsters were made during its entire production with the 1957 model being one of my personal favorites. Known as a race car for the street, it’s one of those elegant vintage automobiles that turns heads wherever it goes. If you’re a big fan of classic roadsters, the 300SL is quite possibly the pick for you.
Mercedes-Benz SL R107
Some might ask why the R107 is listed, but the fact is it was one of the most popular convertibles ever manufactured. We like it because it has the charm of a time when modern cars were in development but at a time when family values were still something most Americans held dear. A great car for the discerning gentleman on a budget, the R107 convertible is unselfish with its four seats and yet still debonair with its classic lines and strong styling. For the young executive, it’s a great pick that you’ll be sure to adore.
Jaguar XK-140 Roadster
The Jaguar XK-140 Roadster is my favorite vintage roadster on the used market today. The successor to the XK-120, it was produced between 1954 and 1957 for the British racing enthusiast. Today, it’s revered amongst the pinnacle of young aristocrats from second and third generation wealth. Unlike the Bugatti Veyron’s and Ferrari’s of Miami’s elite, this is the car chosen by the young heir from upstate New York as his weekend car that gets him to the summer home in Southampton. While supercars are a dime a dozen in places like Los Angeles and Miami, it’s a car like the Jaguar XK-140 that will get you noticed in the crowd.
Alfa Romeo Spider
Its long history dates back to 1966 when it was first produced. Thanks to record sales and popularity, it continued to hit the new car market all the way to 1994 before it became a classic car for the collector.
Over three decades, the car barely changed with the exception of a few minor aesthetic and mechanical alterations. Widely considered one of the most popular convertibles for the distinguished European, it also holds a special place in North America due to its rarity on today’s open road. A true statement of elegance and refinement, Alfa Romeo has long been considered a prime example of the ideal car for the dapper dandy and the Spider is no exception to that rule.
Duesenberg Model J
If you’re a fan of true classics and automobiles from pre-WWII, the Duesenberg Model J might be the pick for you. Introduced to the distinguished aristocrat in 1928, this is the classic Gatsby-style car for any man wearing a boater hat in the summer. If you enjoy dressing for the occasion and take part in vintage events, the Duesenberg Model J is a great option for the dandy looking to make an impression. Just don’t buy it as your main form of transportation. This is more of the car that comes out of the garage on the occasional weekend for short trips on well-manicured roads.
Ferrari 250 GT SWB California
1959 proved to be a fantastic year for Ferrari when they introduced this incredibly elegant convertible. Coveted by the likes of Alain Delon and James Coburn, it is the epitome of what every sports car from the 1960s should drive like. Fashionable and exhilaratingly fast, it is by and large the most elegant Ferrari for the most discerning gentleman.
Jaguar E-type Series 1 Roadster
In 1961, Jaguar introduced its long front-end roadster known as the E-type Series 1. A high-performance race car, it is widely considered one of the most pinnacle vintage roadsters on the road today. It’s distinct appearance has earned it a spot on many of the top car lists from periodicals such as The Daily Telegraph and Sports Car International. It is an iconic statement of sophisticated power with a refinement unlike any roadster ever produced.
1956 Maserati 200 SI
Provocative, unique and distinctively rounded, the 200SI by Maserati is a track born race car that is rarely seen on the open road today. Despite its rarity, it remains a classic car revered amongst racing aficionados. For the ultimate car collector in a suit, 1956 was a phenomenal year for this contemporary, and almost futuristic automobile. If you’re a fan of classic race cars, consider this Maserati for your collection.
1939 Lagonda V-12 Rapide
Now owned by Aston Martin, Lagonda was one of the original British luxury car manufacturers, and the V-12 Rapide was a phenomenal car produced by them for the most distinguished gentleman. One of the most desirable sports cars of the 1940s, there were only 12 built which has made it quite the collector piece today. If you have the budget and the ability to find one of these rare masterpieces, I urge you to pony up and give it the most shining space in your car port.
For those looking for a new convertible rather than a vintage classic, considered the shorter version of the Jaguar XK. The F-Type is a world-class machine that E-Type collectors will not only respect but marvel at. An exceptional supercar, it offers the driver the very latest in technology with the refined sophistication of Jaguar’s rich history and design. If you’re interested in a well-priced machine sure to be considered a classic in the years to come, the F-Type might be the pick for you.
Shelby Cobra 289
What do you get when you cross an English sports car with an American muscle car? The Shelby Cobra. The world’s first English/American hybrid, the Shelby Cobra 289 is widely considered one of the most collectable sports cars in the history of motorized vehicles. With some selling for million dollar price tags; if you happen to have the funds to acquire a classic Shelby Cobra you won’t regret it. If you’re looking for a classic Ford without the brawny definition of a Mustang, the Shelby Cobra is probably the car for you.
1957 Porsche 356 A Speedster
Completely unique compared to the aesthetic details of the modern day Porsche, the Porsche 356 A Speedster is every Porsche lovers dream car. For those tired of the constant barrage of the 911 and Boxsters owned by midlife-crisis-affected executives and blue collar speed demons, the classic 356 A Speedster or Cabriolet is a prime example of what elegance in a Porsche can and should look like.
Bentley Grand Convertible
Bentley rarely releases convertibles but when they do they make a point of ensuring that they are some of the best looking convertibles on the market. Bentley’s new Grand Convertible is nothing short of superlative. It’s regal lines and defining characteristics make it one of the most elegant and graceful convertibles on the market. If speed isn’t your thing, but you still enjoy the wind in your hair, the Grand Convertible is probably the pick for you. That or consider the Rolls Royce Phantom Drophead Coupé listed below. Be sure to check out our in-depth guide on Bentley Motorcars.
If you’re an American and grew up watching some of the finer television shows about classic American family values, you know the nostalgic feeling you get every time you see a 1958 Corvette. Unlike today’s Corvette geared towards the young ruffian, this was a family man’s car. Of course he rarely drove it with his kids in tow, but it became the weekend vehicle for dates with his wife and the car that sat proudly in the driveway as his teenage son washed it for 10 cents to go to the malt shop on a Friday night with friends. It wasn’t only about driving the car, but it was about what the car represented. Even if it only just sat in the driveway. Classic red and white was the American standard, and the 1958 Corvette is about as Americana as it gets. If you’re a suburban gentleman who enjoys the nostalgia of America’s yesteryear, this might be the car for you.
1965 Ford Mustang
Some of the most elegant men enjoy the most masculine activities. For those, the Ford Mustang is the pinnacle of America’s muscle cars. If you looked at some of the other cars on this list and thought they were too feminine, the Mustang is probably your cup of tea. Strong lines mixed with the power of a wild stallion, the classic Mustangs from the mid-1960s are a perfect tribute to what has become one of America’s finest muscle cars. A few years ago on a family trip to California, my wife and I rented a new Mustang convertible. Despite thinking it was too Herculean for our tastes, we quickly grew to love it. There was something powerfully American about driving it down the coast, and it opened us up to the idea that a convertible didn’t need to be graceful to be respected. In fact, whenever I see a Mustang convertible on the road, it brings back fond memories. I look forward to renting one again shortly.
1965 Aston Martin DB5 Vantage convertible
Just 123 DB5 convertibles were made, and only 12 were Vantage powered. The classic James Bond style car, the DB5 convertible, is a true statement of sophisticated elegance for the most discerning gentleman. If you’re fancy yourself a James Bond car and are looking for a topless version, this is your pick.
Rolls Royce Phantom Drophead Coupé
Still refined, yet not nearly as formal, the Drophead Coupé is a more sociable expression of the quality that Rolls Royce stands for. Inspired by the J-class racing yachts of the 1930s, this is the ideal convertible for any yachting enthusiast looking for a new car for the summer. Masculine and yet intimate, it is an ideal pick for the gentleman with the most sophisticated tastes.
We hope you’ve enjoyed our list of the top convertibles for the most discerning gentleman. We look forward to hearing your contributions and what you think is the best convertible for the dapper dandy.