Born in Port-au-Prince, Woolley began his studies in his native city with Carmen Brouard (piano and harmony), Élisabeth de Pesquidoux-Mahy (singing), Werner Jaegerhuber (German opera/lieder), Raoul Nargys (acting), and Henriette Perret-Duplessis (singing). After working for a few years as a choirmaster at a church in Port-au-Prince, he moved to Montreal in 1938 at the age of 22 where he studied singing with Salvator Issaurel from the time of his arrival through 1944. He then entered the Conservatoire national de musique where he earned a Doctor of Music in 1947 after writing his thesis "La phonétique appliquée à l'art du chant". At the conservatoire he was an organ student of Eugène Lapierre and a piano pupil of Edmond Trudel.
