Five convertibles for less than $50,000 – and five where price is no object

Price: $25,995

Horsepower: 160

Pros: Resurrecting a classic isn’t easy, but Fiat’s designers did an amazing job, capturing the spirit of the original 500 (a 1950s micro car) to create a modern version that combines high style with everyday functionality. The Abarth is the sports car of the Fiat 500 lineup, with extra power, fatter tires and crisper suspension. The convertible top is really a glorified sunroof – it opens wide, but the roof’s steel edge remains in place. This creates a strong structure, enhances rollover protection, and limits the amount of wind you’ll get in your hair. The 500 Abarth‘s style is has timeless: style: the body is cute and rounded, the dash is painted, and the shifter juts out like an umbrella handle. Close your eyes and pretend you’re in Rome.

Cons: They’ll make fun of you at NASCAR events.

The Actor, Clothing Style or Event This Car Brings to Mind: Audrey Hepburn in Roman Holiday

Price: $27,999

Horsepower: 305

Pros: If you watch Mad Men, you’ll understand the Ford Mustang’s appeal. This is the car that launched the pony car movement, and changed car marketing forever by selling an indelible image of youth and style. The 2014 convertible is true to the spirit of its ancestors, combining muscle with panache and affordability. The new Mustang is available with a series of engines (including a blockbuster, supercharged V-8 that makes 631 horsepower) but the V-6 version is all you really need for top-down fun. The Mustang is the spirit of 1960s America, expressed in steel and rubber.

Cons: Bring a hat – it’s windy in the back seat.

Brings to mind: The Sexual Revolution.

Price: $29,250

Horsepower: 167

Pros: The MX-5 is one of the finest two-seat roadsters ever built. It was inspired by 1960s British roadsters like the MGB and Lotus Elan, but the MX-5 changed the game by bringing Japanese engineering and quality control to the affordable sports car market. The MX-5 has been called “the MGB that doesn’t leak oil.” You can get the MX-5 with an automatic transmission and a power-folding steel top, but purists will opt for a manual top and transmission, which cut weight and add driving pleasure. Drive an MX-5 and you’ll understand how Japan conquered the sports car market.

Cons: A hockey bag will barely fit.

Brings to mind: Mila Kunis.

Price: $34,150

Horsepower: 189

Pros: The Mini Cooper S is the very definition of fun – it’s compact and quick, with plenty of torque, slick suspension and a joyously accurate shifter. The Mini comes in two topless versions – the Convertible and the Roadster. The Roadster is better looking, but sacrifices its back seat for a stylish tail section. This isn’t really a problem – if you wanted practicality, you wouldn’t be buying a drop-top car in the first place, and no one will want to ride in that back seat, anyway. The Cooper S Roadster is an excellent package that combines strong performance with good fuel economy.

Cons: It’s a little too cute for some.

Brings to mind: The lead singer of One Direction getting his hair styled.

Price: $38,790

Horsepower: 426

Pros: The Camaro is an American icon, with a history that reaches back to the 1960s. It conjures up images of drag strips, nighttime cruises, and Bruce Springsteen music blaring through speakers thumping with extra bass. The original Camaro was a competitor to the Mustang, and the new one plays the same role. But the new Camaro has features that make the original look like a stone-age contraption – the live rear axle is gone, replaced with an independent rear suspension that works beautifully on a twisting, bumpy road. The Camaro’s styling is a hate it or love it proposition, with a flat hood, sharp lines, and cut-down windows that give it the menacing look of a rolling machine-gun nest. In the hardtop version, those low windows hurt visibility, but the convertible offers a panoramic view – at least until you put the top up.

Cons: It starred in Transformers.

Brings to mind: Burt Reynolds before his hip replacement.

Price: $57,400

Horsepower: 306

Pros: If you want a slick, beautifully packaged convertible that will seat four, the Lexus IS 350C is hard to beat. The metal top folds like mechanized origami, and the 350C is rear-wheel drive, which optimizes steering feel. The 350’s controls work with silken precision, and your chances of a trouble-free experience are good – Lexus is ranked consistently high for engineering, build quality and reliability. The 350C’s style is corporate/conservative – if it were a suit, it would be black, worn with matching belt and shoes.

Cons: That cool folding top kills trunk space.

Brings to mind: That guy whose name you can never remember.

Price: $58,600

Horsepower: 265

Pros: Porsche’s reputation for building solid, great-handling sports cars is well deserved. Although German car snobs knock it because it isn’t a 911, the Boxster is a wonderful package, with a perfect blend of power, handling and value. The Boxster’s steering is nicely weighted, and the flat-six motor sounds like nothing else (it sounds even better if you get the sport exhaust system and keep the top down). The Boxster’s folding top seals perfectly, and goes up and down in seconds. It’s a personal, engaging machine that ticks every box on the list of attributes that make a great sports car. If you want to spend more, buy the Boxster S, which has 50 more horsepower. But on the street, the base model’s power is all you need. Most buyers opt for the paddle-shift PDK transmission, but the six-speed manual is less expensive, and feels great.

Cons: Your Porsche buddies will mock you for not buying a 911.

Brings to mind: Leather short pants with suspenders and stag-horn decoration.

Price: $76,900

Horsepower: 340

Pros: Choosing a convertible is like finding a spouse – all things being equal, good looks are a bonus. The F-Type is the supermodel of sports cars, with lines that stop onlookers in their tracks. Its elegance is due to a combination of inspired design and corporate DNA – this car is the direct descendant of Jaguar’s legendary E-Type, which hit the market in 1961, and was declared “the most beautiful car ever made” by no less than Enzo Ferrari. The F-Type is the first modern Jaguar that can be legitimately compared to its 1960s’ forebear, and it’s a much better car than the old one could ever hope to be (modern engineering and manufacturing has its benefits).

Cons: All heads will turn – but it will be for your car, not you.

Brings to mind: A Victoria’s Secret fashion show.

Price: $305,000

Horsepower: 641

Pros: If you want a convertible with ultimate performance and tech-cred, this is it. Crafted in McLaren’s clean room of a factory, the 650S Spider is less a car than an otherworldly mechanical apparition. Beneath the carbon skin of the 650S is a collection of high-tech mechanicals, a flowing composite chassis, and enough computer code to run America’s National Security Agency. This technology is used to deliver one of the world’s great driving experiences – with 641 horsepower, carbon brakes and massive cornering power, the McLaren’s limits will exceed your own. With the top down, and the 3.8-litre V-8 shrieking away millimetres from your skull, this will be a ride you won’t forget. Luggage space is limited, but who cares?

Cons: It can do more than 330 km/h. You can’t.

Brings to mind: RoboCop.

Price: $315,200

Horsepower: 565

Pros: The Vanquish epitomizes the Aston Martin ethos, which is based on bolting a massive engine into a small but substantial car (there’s a reason why Aston Martin is the signature car of James Bond). The Vanquish has the glinting presence of a super-sized medieval broadsword. It’s beefy. You ride in a compact, leather-lined interior, looking out over the long hood, as if you were commanding a small but mighty warship. The Vanquish’s convertible top can be operated at speeds up to 50 km/h. If you can find a long enough road, top speed is 295 km/h.

Cons: Everyone will think you’re James Bond. You’re not.

Brings to mind: The Battle of Hastings.