The Jeep Grand Wagoneer’s design virtually never changed, making it one of the few automobiles that connected entire generations of people.


Kelly and I had long since fallen in love with the classic lines of the Grand Wagoneer. The legacy of the car is renowned; many credit the Wagoneer for inspiring the concept of a luxury SUV. It competed with Range Rovers because it offered finer appointments to a truck-based platform more often associated with rugged austerity. Wagoneers were a staple of WASP culture, the preppy automobile of choice for lawyers and doctors and their private school kids.

These days, the cars are symbols of a vintage culture that floats further and further away. Put a Christmas tree on the roof rack and a wreath on the front grill, and you have enough Lands End kitsch that you can probably leave the kids out of your holiday card photo. I’ve always wondered about who drives these things and what kinds of lifestyles they might lead.

So when we spotted a Grand Wagoneer around town, it was interesting to see not just the car but who was behind the wheel.

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