All Oldsmobiles were completely restyled for 1959, with the 88 series given longer, lower and wider styling on a GM B-body chassis. The 88 shared its appearance with the top-model Oldsmobile 98. Styling highlights for the new models, promoted as the "Linear Look," included six-window styling on four-door pillared sedans, glassy semi-fastback rooflines on Holiday coupes and flat-blade rooflines with thin windshield and C-pillars on Holiday sedans which created a large open greenhouse effect. Two-door hardtops were called a "Scenicoupe," 4-door hardtops "Sport Sedan." While many 1959 model cars featured bigger and sharper fins, Olds flattened theirs horizontally and reduced chrome from 1958 for a much cleaner look. Wheelbases on 88 models increased by one inch to 123 inches (3,124 mm).
A larger 394 cubic-inch Rocket V8 with four-barrel carburation rated at 315 hp (235 kW) was standard on the Super 88. The lower-priced Dynamic 88 retained the two-barrel 265 hp (198 kW) 371 cubic-inch '57–58 Rocket V8, with a 300 hp (220 kW) four-barrel version optional.
A simpler but bold new grille and revised rear design with even flatter tailfins and new taillights highlighted the 1960 makeover. Power for Super 88 models remained the same, while Dynamic 88s had their 371 ci Rocket V8 detuned to 240 hp (179 kW), where a lower compression ratio accommodated lower-priced regular gasoline. Other changes included a revised instrument panel and a slimmer transmission tunnel for improved interior space.