5 Classic Convertibles Cheaper Than A New Subaru Outback Loaded
The classic car market has rarely been stronger, as enthusiasts aim to recapture the character and excitement of the legendary analog cars they grew up with and aspired to own. In an era of increasing electrification, digitalization and ever-more sanitized driving experiences, there’s a growing appetite for cars that are simpler, more visceral and mechanical. This has led to a resurgence of interest in enthusiast cars from the 1970s through the 1990s.
While prices for classic performance cars have gone through the roof, there’s still exceptional value to be found, particularly if you’re looking for that carefree wind-in-the-hair experience that only a classic convertible can deliver. In fact, you can buy five running, driving classic drop-tops for less than the price of one fully loaded $45,790 2026 Subaru Outback Touring (non-XT).
Here are five affordable classics that could add some open-air fun to your collection without breaking the bank.
5
Chrysler LeBaron 2nd Gen Convertible (1982-1986)
Average Used Value: $5,937
The Chrysler LeBaron was the car that brought factory-built American convertibles back into vogue in the early 1980s after the segment faded almost completely over the prior decade due to a combination of safety concerns related to convertibles, increasing regulations and a growing preference for hard-top coupes and the comfort of air-conditioning.
Produced from 1982 to 1986 as part of the second-generation LeBaron range, the convertible was a two-door, four-seat drop-top that exudes 1980s charm and quirkiness. However, relying on front-wheel drive and a variety of four-cylinder engines during its six-year production run, the LeBaron is undeniably a sedate cruiser that focused on style rather than performance.
The standard engine was a 2.2-liter 84-87 hp unit with a four-speed manual transmission initially, followed by a five-speed from 1983. Customers could also opt for a 2.6-liter engine (available in automatic only), which offered only slightly more power at 92 hp, with outputs of both engines climbing marginally over time. The 2.6L engine was dropped in favor of Chrysler’s 100 hp 2.5L unit for the final production year in 1986, along with electronic fuel injection being fitted across the range.
A turbocharged 142 hp 2.2L variant was added to the lineup in 1984, delivering considerably more performance in both manual and automatic. This makes it the infinitely more appealing choice as a usable classic.
Just over 75,000 LeBaron convertibles were produced over the five years, the majority of which were base specification. However, for the first production year, the more luxurious Medallion trim outsold the base spec by more than three to one, before being replaced in 1983 by the upscale Town & Country. This makes the Medallion a strong shortlist candidate as the more feature-rich vehicle during the important first production year.
Over the ensuing four years, the Town & Country was far more exclusive and rare, with a total of 3,721 units being built. It stood out with the faux wood grain exterior that harked back to Chrysler’s Town & Country woodies of the 1940s, a gaudy and questionable choice for a trend-setting convertible. However, it remained part of the lineup until production ended in 1986.
Customers could also select the fully loaded Mark Cross luxury package as an option on the base model, while it was standard on the Town & Country. Depending on model and year, this includes an extensive range of upmarket features such as leather/vinyl bucket seats, specially upholstered door trims, leather-wrapped steering wheel, an electronic instrument cluster, power steering, power brakes, power windows, power-operated roof, cruise control and air-conditioning.
Although there isn’t an abundance of LeBaron convertibles available for sale at any point, they regularly appear at auctions and private listings. Classic.com lists an average price of $5,937, which gets you into a decent original car that you can simply drive and enjoy, such as a 43,000-mile example that was recently sold for $6,500.
A variety of cars can be found at both ends of the price spectrum, ranging from a 70,000-mile 1983 Town & Country that recently sold for just $3,250, to high-end collector-quality examples stretching to $29,980 for a 1982 19,000-miler, or up to $37,980 for a 1985 model with just 5,394 miles on the clock.
4
Ford Mustang GT 3rd Gen Convertible (1983-1985)
Average Used Value: $12,614
The first-generation Ford Mustang was an industry-defining car when it debuted in 1964, combining compact dimensions, sporty styling, and affordable pricing that made it the quintessential American pony car.
With well over 10-million Mustangs produced over the past 62 years, it’s no surprise that it has consistently been America’s best-selling sports car. This gives enthusiasts a huge amount of choice when it comes to buying a usable classic covering the seven generations, spanning from 1964 to the latest iteration that was launched in 2024.
After the massive success of the first gen, the 1974-1978 Mustang II was a victim of the global oil crisis that led to manufacturers focusing on making smaller and more fuel-efficient cars. Fortunately, the legendary pony car made a spectacular return to form with the third-generation Fox body, which was produced from 1979 to 1993.
Crucially, in 1983, it also reintroduced the convertible body style that had been absent since the end of the first generation a decade earlier. It had all the muscular design features that defined the Fox body Mustang, with the aggressive angular design and those distinctive four headlights.
What makes these Mustang GTs particularly appealing is that they were the last of the carburetor-fed Windsor 302 cu-in (5.0L) V8s before sequential EFI was introduced in 1986. Power was initially rated at 170 hp for the first two years but was pushed up to 210 hp for the 1985 model year, making this the pick of the bunch for driving thrills, especially paired with the five-speed manual. The stricter emissions regulations saw the power output of the EFI-equipped V8 drop to 200 hp in 1986.
The Windsor V8 is renowned as one of Ford’s most durable engines and parts availability remains excellent, but seeking out a clean original or sympathetically restored example will be the biggest challenge for an enthusiast looking for an enjoyable classic. Based on production databases and specialist registries, total production is estimated at approximately 12,800 vehicles from 1983-85, with less than 1,000 units built in the first year.
Classic.com shows the average price in the $12,000 range, with seemingly decent examples available for under $10,000 with as little as 41,000 miles, or a one-owner 1985 car with 90,000 miles – a car that has been driven, and deserves to clock up more open-air mileage in the hands of a caring owner.
Lower-mileage cars command more money, ranging from $15,000 to $17,000, or immaculate high-end little-used examples valued at well over $30,000 that will likely just form part of a collection rather than being driven and thoroughly enjoyed.
3
Oldsmobile Cutlass Supreme 5th Gen Convertible (1990-1995)
Average Used Value: $7,110
For a more modern, distinctly 1990s take on the open-top theme, the Oldsmobile Cutlass Supreme Convertible is worth adding to the list. Based on the fifth and final generation of the Cutlass Supreme (1988-1997), the spacious five-seat convertible model was sold from 1990 to 1995, with approximately 25,000 vehicles produced.
As with the Chrysler LeBaron and Ford Mustang GT, General Motors had largely abandoned convertibles under the threat of a government ban, but the Cutlass Supreme was one of the few exceptions. However, unlike its factory-built rivals, the Oldsmobile drop-top was a collaboration with specialty coach builder Cars & Concepts which handled the engineering, structural reinforcement and soft-top integration. As factory-backed models, they were sold through GM/Oldsmobile dealers.
The Cutlass Supreme’s convertible story actually starts a couple of years earlier, in 1988, as it served as the Official Pace Car of the 1988 Indianapolis 500. These were hand-built prototypes produced by Cars & Concepts, comprising a handful of turbocharged four-cylinder track pace cars, along with 50 additional replica cars (reportedly fitted with a 2.8L V6) produced for the Indy 500 Festival and other supporting roles. Oldsmobile also manufactured 200 Cutlass Supreme hardtop coupes with Pace Car graphics.
This high-profile marketing platform generated plenty of interest for the production Cutlass Supreme Convertible which was launched in 1990. It was powered by a 140 hp pushrod 3.1-liter V6, delivering power to the front wheels via a four-speed automatic. From 1993, a more advanced twin-cam 3.4-liter V6 was added as a high-performance option, producing a far livelier 210 hp.
Numerous trim and specification upgrades were applied over the years, including the addition of a driver-side airbag and ABS as standard in 1994. A redesigned cabin and dashboard were highlights of the final model year, along with dual front airbags and the controversial door-mounted seatbelts being moved to the B-pillar loop.
With an average price pegged at around $7,100 according to Classic.com, there is merit in looking for the early 1990 launch models, which typically sell for between $5,000-$7,300 for a solid, readily usable classic. Brand loyalists are likely to favor later models, particularly the final production year, with prices ranging up to $15,700 for a well-kept, low-mileage car with the more powerful 3.4L V6.
2
Fiat 124 Sport Spider (1966-1985)
Average Used Value: $11,008
The Italians know how to do style, and Fiat’s 124 Sport Spider proves that in abundance. Although it was based on Fiat’s humble four-door sedan, renowned Italian design house Pininfarina transformed the boxy and rather bland family car into a genuinely elegant and enduring two-seat sports car that remains eye-catching today.
The car had an amazing production run, with the first units coming off the line in Turin in 1966 and production eventually ending in 1985. Notably, the car was sold as the Fiat 124 Sport Spider until 1979 when it was rebadged as Spider 2000. Fiat production ended in 1982, but Pininfarina continued producing it for another three years under its own brand as the Pininfarina Spider Azzurra for the North American market, and the Spider Europa for Europe.
It was compact and nimble, thanks to a curb weight of just 2,080 lb for the early models (around 700 lb lighter than the early six-cylinder Mustang). The Fiat’s weight climbed only marginally over subsequent model upgrades, ending just short of 2,300 lb in the final versions.
The Sport Spider had relatively straightforward mechanicals that made it engaging and entertaining to drive, with the free-revving double overhead cam four-cylinder engines used throughout its production giving the car considerably more sporting character than its relatively modest power figures suggest. It’s a theme that has been replicated by the ever-popular Mazda MX-5/Miata.
Engine performance increased from the 90 hp delivered by the initial 1.4-liter unit to a peak 118 hp delivered by the upgraded 1.8-liter and subsequent 2.0-liter models that were available from 1972-1980. Over the remaining production, power was rated at 102 hp for the 2.0L engine. US emissions regulations curtailed performance to 87-92 hp throughout the 1970s, but this was later pushed up to 102 hp with the introduction of fuel injection in the Spider 2000.
Fiat offered its US customers a locally developed 120 hp turbocharged version of the 2.0L engine in 1981 and 1982, while supercharging was on offer across the Atlantic during the two final production years of the Pininfarina Spider Europa.
Key innovations that made the rear-wheel-drive Sport Spider appealing from a driver’s perspective were all-round disc brakes, independent front suspension and a five-speed manual gearbox (from around 1968). An optional three-speed gearbox sourced from General Motors was available in the US from 1979 to 1985, but the overwhelming preference was for the manual – and rightly so.
As with most Italian cars of the period, the mechanicals are strong, but rust is a major problem – so any purchasing decision needs to be backed up by an in-depth inspection, ideally by an Italian car specialist. Although US cars are generally easily identified by the large black bumpers that were required to meet federal crash regulations from the mid-1970s, the European slim chrome bumpers are often retrofitted to enhance the car’s sleek appearance.
The US was the 124 Sport Spider’s biggest market by far, accounting for approximately 170,000 (85%) of the almost 200,000 units built, according to Stellantis. When the modern Fiat 124 Spider was launched in 2015, based on the Mazda MX-5, the company estimated that there were still nearly 8,000 of the original models registered in the US.
Accordingly, finding a car to suit your requirements and budget is relatively straightforward with parts availability not a major concern. With an average price around the $11,000 mark, you can readily find a project car for as little as $4,200, or the rare turbo model for under $10,000. Expect to pay $15,000 to $18,000 for an immaculate or restored car such as the 1984 Pininfarina Azzura or a completely refurbished early 1973 model.
1
Triumph TR7 Drophead Coupe (1979-1981)
Average Used Value: $6,852
Finally, for something unashamedly wedge-shaped, quirky and distinctly Seventies British, there’s the Triumph TR7 convertible (commonly referred to as the Triumph Wedge). Although the TR7 Fixed Head Coupe (FHC) was originally launched in 1975, the convertible, or Drophead Coupe (DHC) as it was officially titled, was only produced from 1979 to 1981.
Of the total TR7 production of approximately 115,000 cars, an estimated 28,864 convertibles were reportedly built according to enthusiast forums. Interestingly, despite being designed and manufactured in the UK, the convertible was first launched in the US in 1979, and then only a year later in its home market.
The TR7 was essentially the antithesis of anything Triumph or the other British manufacturers had produced before. Where the TR6 followed the mold of a classic rounded two-seat roadster, the TR7 set out to modernize the formula. It featured an angular wedge shape with distinctive retractable headlights that were designed to reinforce the car’s low-slung stance. This thoroughly unique design is what makes the TR7 an interesting choice for a classic convertible.
Performance is laid-back rather than spirited, as the 2.0-liter carburetor-fed four-cylinder engine produced just 92 hp in US specification compared to the higher-compression UK/EU models that had around 102 hp. With a curb weight of 2,350 lb, a 0-60 mph time of 11-12 seconds and a top speed of just 105 mph, this isn’t a car to blow your socks off. At least it was offered with a five-speed manual as standard, but a truly pedestrian three-speed automatic was available as an option and is best avoided.
As with the Fiat 124 Sport Spider, the large and ungainly federal impact bumpers are typically a key identifier for US models, but these also had the lower-output engines. European LHD or UK RHD cars will be more appealing from a design and performance perspective.
Most products within the British Leyland stable were plagued by quality and reliability issues throughout the Seventies and Eighties, and the TR7 is no exception. Electrical problems have always been one of the car’s biggest weaknesses, as is rust. Although the engine is fairly robust, the cars often experienced overheating issues.
Accordingly, a well sorted and fully inspected example is a must, especially as production numbers were relatively low for the DHC/convertible and finding parts will be difficult. Looking at cars available or sold this year on Bring a Trailer, a reasonable driver that would benefit from some cosmetic work can be found for around $4,700, stretching to $6,900 for a neat partially refurbished mid-range 42,000-miler. A remarkable 600-mile 1981 TR7 DHC was sold on BaT for $16,250.
If your budget extends a bit further, the TR8 powered by the ubiquitous Buick/Rover 3.5-liter V8 is definitely a candidate too. It was basically the V8 version of the TR7 with 133 hp, 0-60 in 8.4 seconds and a 120-mph top speed. However, only about 2,600 cars were built before production of the TR7 and TR8 ended in 1981, making them much scarcer and pricier, ranging from around $10,000 to $25,000.
Bring a Trailer, Mecum, Hagerty, Fiat, Ford, Stellantis, Classic.com, Triumph Owners Clubs
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