The ‘Grandpa Cars’ That Are Secretly Cool Now

Not all classics come from racetracks or exotic garages. Some of the coolest vintage cars today were once dismissed as "grandpa cars" — big, soft, and often overlooked. But the tides are turning. These sleeper classics are making a surprising comeback among collectors, hipsters, and retro-lovers alike. With their old-school charm, bulletproof reliability, and unexpected swagger, these are the old man cars that are stylish now and definitely worth your attention.

Buick Roadmaster Estate Wagon (1991–1996)

Once seen as the ultimate retirement cruiser, the Buick Roadmaster Estate Wagon is now an icon of 1990s Americana. Powered by a Corvette-derived LT1 V8 in later models, it packs surprising muscle under its massive hood. With woodgrain siding, rear-facing third-row seats, and floaty comfort, it delivers retro charm like few others. Enthusiasts love it for road trips, surf builds, and ironic cool factor. Despite its size, the Roadmaster offers decent highway fuel economy and an incredibly smooth ride. It’s also one of the few wagons that can tow, haul, and look nostalgic doing it. It's one of the best sleeper classic cars under $10k, and values are on the rise.

Lincoln Town Car (1988–1997)

If you want plush comfort and overbuilt quality, the Lincoln Town Car delivers. This full-size sedan was long the choice of executives and grandparents alike. Today, it’s being rediscovered for its unmistakable boxy silhouette, pillow-soft ride, and durability that borders on legendary. The rear-wheel-drive platform and 4.6L V8 make it an easy platform for customizing or cruising. With ample chrome, a V8 under the hood, and surprisingly good aftermarket support, it's no wonder the Town Car is finding a second life among younger collectors. Fleet-kept examples are still surprisingly affordable, making it one of the best entry points into classic American luxury.

Mercedes-Benz W123 (1976–1985)

Long considered the ultimate "sensible car," the W123 Mercedes sedans and wagons are now appreciated for their timeless design and indestructible engineering. Diesel variants are known to go well past half a million miles, and their build quality rivals anything modern. Hipsters, collectors, and DIY enthusiasts have all fallen in love with the W123's analog feel and classic lines. With features like vacuum-powered accessories and bank-vault doors, it’s a tactile throwback to when Mercedes built cars to last a lifetime. It's become one of the most stylish retro luxury cars you can still buy affordably — and prices are climbing.

Cadillac Sedan DeVille (1980s–1990s)

The Cadillac nameplate once defined American luxury, and the Sedan DeVille of the '80s and '90s still holds that legacy. With acres of sheet metal, plush velour or leather interiors, and digital dashboards ahead of their time, these Caddies scream retro opulence. Later models featured front-wheel drive, making them easier to live with in urban settings. They're turning heads again at shows and in pop culture, often customized into lowriders or kept bone stock for nostalgic effect. The DeVille's smooth ride and presence make it a stand-out at cruise nights and classic car meets.

Volvo 240 (1975–1993)

Yes, the Volvo 240 was the ultimate sensible Swedish brick, but its square lines and Spartan vibe have become unexpectedly trendy. Beloved for its legendary safety, simple mechanics, and indestructibility, the 240 has become a cult favorite. The 240's rear-wheel-drive layout and strong aftermarket support have even made it popular among tuners. Its design screams “practical,” but that’s exactly what makes it cool today — it’s a retro machine that just keeps running. From hip city dwellers to classic car purists, everyone seems to want one.

Oldsmobile 98 Regency (1980s)

Overshadowed by Cadillacs and Buicks, the Oldsmobile 98 was once the peak of comfort for GM's elder statesmen. But it had real presence: a long wheelbase, padded roof, opera lights, and a cushy ride that could absorb potholes like clouds. Inside, you’d find plush seats, woodgrain trim, and digital gauges. Underneath, it shares a platform with other GM classics, making parts easy to find and repairs manageable. As more people look for unique, full-size classic American sedans, the 98 Regency is quietly building a cult following among retro American luxury enthusiasts.

Toyota Cressida (1978–1992)

The Toyota Cressida was Japan’s understated luxury sedan before Lexus arrived. With rear-wheel drive, inline-six powerplants (some shared with the Supra), and Toyota's rock-solid reliability, it's a fantastic blend of performance and comfort. Cressidas are now popular among drift and JDM communities, with clean examples gaining value fast. Earlier models came with luxurious appointments like power everything, plush velour interiors, and even optional automatic climate control. It’s a hidden gem among classic JDM cars with vintage appeal and daily driver potential, especially for those who want something different than a traditional muscle car or European import.

Today’s grandpa cars are tomorrow’s collectibles. As trends shift and nostalgia grows, these underrated vintage cruisers are finding new appreciation across generations. Whether you're into sleeper classics, retro luxury, or just want a cool vintage daily driver, these once-overlooked models are ripe for discovery. Get one before the secret’s out.

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