Orpen was born in Blackrock, near Dublin. He studied at the Metropolitan School of Art in Dublin from his early teens before moving to London in 1897. Orpen subsequently studied at the Slade School of Fine Art for two years, where he became friends with the artist Augustus John. He later went on to become one of the most successful society portraitists of his day, commanding huge sums of money for his work. In 1917 Orpen worked as an Official War Artist in France.