One of Earth's most fundamental climate shifts - the greenhouse-icehouse transition 34 Ma ago - initiated Antarctic ice-sheet build-up, influencing global climate until today. However, the extent of the ice sheet during the Early Oligocene Glacial Maximum (~33.7-33.2 Ma) that immediately followed this transition, a critical knowledge gap for assessing feedbacks between permanently glaciated areas and early Cenozoic global climate reorganization, is uncertain. Here, we present shallow-marine drilling data constraining earliest Oligocene environmental conditions on West Antarctica's Pacific margin - a key region for understanding Antarctic ice sheet-evolution. These data indicate a cool-temperate environment, with mild ocean and air temperatures preventing West Antarctic Ice Sheet formation. Climate-ice sheet modeling corroborates a highly asymmetric Antarctic ice sheet, thereby revealing its differential regional response to past and future climatic change.