Through his childhood, Sheehy Skeffington circulated through a number of prestigious schools, including time spent at Boyland School in Santa Barbara, California and in Dublin, at Sandford Park School, a non-denominational school selected by his mother in the face of strong criticism from her Catholic and Republican friends. His cousin, the diplomat, writer and politician Conor Cruise O'Brien, was a pupil there at the same time. His mother deliberated choose schools viewed as socially progressive for Owen, something that instilled in him lifelong values.