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Five classic cars worth buying and keeping for the long term

From American convertibles to Italian beach runabouts, these five classics combine rarity, desirability and investment potential for collectors willing to seek out the best examples.

By Chris Wilson Updated
1960 Maserati 5000 GT by Touring
1960 Maserati 5000 GT by Touring James Bond / CC BY 2.0

Collectors chasing more than just nostalgia often look for classic cars with a blend of rarity, style and the potential to hold or appreciate in value. Five models stand out for buyers willing to invest now and hold for the long term, provided they can secure a sound example.

1958 Buick Limited Convertible: Fifties luxury, limited supply

The 1958 Buick Limited Convertible sits at the rare end of American Fifties luxury. With production numbers far lower than the more commonly seen Cadillac Eldorado, the Limited combines dramatic styling, extensive chrome and a 364 cu in V8. Surviving examples are highly sought after. Values in the mid-20100s ranged from $90,000 to $120,000 for a well-restored car, reflecting both its scarcity and its status among US collectors.

1958 Buick Limited Convertible
Rare Fifties American luxury with dramatic styling.

1947 Chrysler Town & Country Convertible: classic American 'woody'

Chrysler’s Town & Country Convertible from 1947 is one of the most recognisable postwar American convertibles thanks to its timber-framed bodywork. Built in limited numbers, it was expensive even in its day. Today, it appeals to buyers after open-air touring and classic design. Expect to pay $100,000 to $150,000 for a strong example. Its combination of rarity, craftsmanship and period charm keeps it in demand among serious collectors.

1959 Fiat Jolly: the beach car with Italian flair

The Fiat Jolly, produced in 1959, is the most unconventional car on this list. Based on the Fiat 500 or 600 chassis, the Jolly was created by Ghia as a low-volume, open-air runabout for resorts and private islands. Its cut-down doors, wicker seats and canopy roof make it instantly recognisable. Few were built and fewer survive, which keeps values strong, typically $50,000 to $100,000. The Jolly’s appeal lies as much in its rarity as in its charm, and it remains a favourite for collectors seeking something different.

1966 Ford Shelby Mustang GT350: a muscle car with pedigree

Shelby’s 1966 GT350 Mustang is often overshadowed by later, more extreme Shelby models, but its blend of performance and provenance gives it lasting appeal. Fitted with a 289 cu in V8 and recognised for its race-bred upgrades, the GT350 was built in limited numbers and carries the Shelby name. Pristine cars were fetching $140,000 to $160,000 in the mid-2010s, a figure reflecting their status among American muscle enthusiasts and collectors. For more on classic Ford performance cars, seePerformance Ford Classic Car Collection Going Under the Hammer.

1959 Cadillac Eldorado Biarritz: American opulence at its peak

No list of collectible American classics is complete without the 1959 Cadillac Eldorado Biarritz. Its tailfins, chrome and sheer scale symbolise late-Fifties US excess. The Eldorado Biarritz was Cadillac’s flagship convertible, with prices for strong examples ranging from $100,000 to $200,000. Its enduring appeal comes from both its design and its position as a cultural icon of the era.

1959 Cadillac Eldorado Biarritz convertible in Warsaw
Flagship American convertible known for its tailfins and chrome.
1947 Chrysler Town & Country at the Blackhawk Museum
Postwar American 'woody' with timber-framed bodywork.
1959 Fiat Jolly in yellow and white, front view
Italian open-air runabout designed by Ghia.
1966 Ford Shelby Mustang GT350 at a car show
Shelby-heritage Mustang with race-bred upgrades.

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