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The Mercedes-Benz W111 was a chassis code given to a range of vehicles produced between 1959 and 1971, including four-door saloons (1959-1968) and two-door coupés and cabriolets (1961 to 1971). Their bodywork featured distinctive tailfins that gave the models their Heckflosse nickname — German for "fintail". Introduced with a 2.2-litre inline-six engine (later also the W110 (entry level : 4-cylinder engine, with the same chassis and bodies; and the W112, a high-end luxury saloon built on the W111 chassis with its body but exclusive features and elaborate appointments. The design of a replacement for the two-door Pontons was the work of engineer Paul Bracq (French engineer who also worked for Peugeot and BMW) , which featured a more square, subtle rear-end treatment, more evocative of the later squarish styling of the subsequent W108/109 than the sharp-edged tailfins of the saloon.
Production began in late 1960, with the coupé making its debut at the 75th anniversary of the opening of Mercedes-Benz Museum in Stuttgart n February of the next year. The convertible followed at the Frankfurt Auto Show a few months later. Almost identical to the coupé, its soft-top roof folded into a recess behind the rear seat and was covered by a tightly fitting leather "boot" in the same color as the seats. Unlike the previous generation of two-door ponton series, the 220SE designation was used for both the coupé and convertible; both received the same version of the 2195 cc M127 engine.
In March 1962, Mercedes-Benz released the exclusive two-door M189-powered 300SE. Like the 300 saloon, it was based on the W111 chassis but shared both Daimler's top-range 2996 cm3 fuel-injected engine and the unique W112 chassis designation, efforts on Mercedes' part to distance it from the maker's modest W110 and W111 lineups and link it to the prestigious W188 300S two-door luxury sports tourer. In summer of 1965 Mercedes-Benz launched replacements for both W111 and W112 saloons, the W108 and W109 respectively. With the tailfin fashion well eroded by the mid 1960s, the new design was based on the restrained W111 coupé, widened and squared off. Work on a future new chassis that would fully replace the Ponton-derived W111/W112 and W108/W109 was well under way. With a concept car of the first S-class was shown in 1967, Daimler declined to develop a two-door W108/W109 vehicle, instead continuing production of the aging W111/W112 with modest changes. The 220SE was superseded in early autumn 1965 by the 250SE, which featured the new 2496 cm3 M129 engine. Since the W108/109 were only available as 4-door models, 2-door W111 and W112 coupés and cabriolets like this 1969 280SE are frequently mistaken for them
In November 1967 the 250 SE was superseded by the 280 SE. It was powered by the new 2778 cc M130 engine. In 1971, the W116 replaced the W108/109 series.