A high-end derivative of the 220 Sedan, the 280 SE was introduced in 1959 featuring its timeless styling and incredible build quality. The basic design and chassis — internally designated W111 — endured for more than a decade. Over its lifetime, the car could be had with one of five single-overhead cam engines: four six-cylinder motors along with a 3.5 Liter V8. Each update brought more horsepower and torque, improving drivability and the feeling of luxury. The V8 was released in the fall of 1969, around a full ten years after the model’s inception. The combination of classic styling of the earlier models and ever more powerful engine options proved irresistible to critics then and now.

A full leather interior with accommodations for four along with a fully lined top in the traditional stacked German cabriolet layout meant the 280 SE Cabriolets could easily be driven all-year ’round. A fully independent suspension with disc brakes at each wheel was standard, further increasing comfort and safety. Due to their complexity, only 13 cars were finished per week on average. For example, each top required roughly sixteen hours of work apiece, with the robust metal framework being entirely concealed from view by a full interior headliner. In total, Mercedes-Benz produced just 1,232 examples between 1969 and 1971. As one of the marque’s last hand-built models, 280 SEs are highly vaunted by collectors and enthusiasts alike.