Bailey received a doctorate of philosophy in art history from Oxford University. Shortly thereafter he was awarded a fellowship at the Getty Museum's paintings department. He found the experience so significant that he decided to pursue museum work instead of academic work.
Bailey started his curatorial career as an assistant curator of European Painting and Sculpture at the Philadelphia Museum of Art, where he worked from 1985 to 1989. In 1989 he began working as curator of European Painting and Sculpture at the Kimbell Art Museum and he was appointed to senior curator there in 1990. In 1995 Bailey began working as chief curator of the National Gallery of Canada, Ottawa, and was appointed Deputy Director and Chief Curator in 1998. In 2000 he became the Chief Curator of The Frick Collection where he would later be promoted to Deputy Director and Peter Jay Sharp Chief Curator. Alongside his curatorial posts he taught graduate seminars in art history at Bryn Mawr College, Columbia University, and the City University of New York Graduate Center.
While at the Frick, Bailey was an inaugural fellow at the Center for Curatorial Leadership beginning in 2008. Bailey credits this program with shifting his aspirations from the curatorial to the directorial. The Center exposed him to his first formal training in management techniques and to the idea that active curators with skills in management, finance, strategy, and diplomacy could play important roles in the future of their institutions. Near the end of his program at the center, Bailey held at a residency at the Louvre, closely observing its director, Henri Loyrette.
From 2013 to 2015, Bailey was the director of the Fine Arts Museums of San Francisco, overseeing both the de Young Museum and the Legion of Honor. In August 2015 Bailey was appointed director of the Morgan Library & Museum.Chevalier de l’Ordre des Arts et des Lettres (1994)
Officier de l’Ordre des Arts et des Lettres (since 2010)
Foundation for Italian Art and Culture Excellency Award (2013)
Bailey, Colin B. (1992). The Loves of the Gods: Mythological Painting from Watteau to David. New York: Rizzoli. ISBN 9780847815210
— (1997). Renoir's Portraits: Impressions of an Age. New Haven: Yale University Press. ISBN 9780300071344
— (2002). Patriotic Taste: Collecting Modern Art in Pre-Revolutionary Paris. New Haven: Yale University Press. ISBN 9780300089868 (Winner of the Jan Mitchell Prize for the History of Art)
— (2006). Building the Frick Collection: An Introduction to the House and Its Collections. New York: Frick Collection in association with Scala. ISBN 9781857593815
— (2009). Watteau to Degas: French Drawings from the Frits Lugt Collection. New York: Frick Collection. ISBN 9780912114453 (co-author with Susan Grace Galassi)
— (2011). Fragonard's Progress of Love at The Frick Collection. New York: Frick Collection. ISBN 9781904832607
— (2012). Renoir, Impressionism and Full-Length Painting. New York: Frick Collection. ISBN 9780300181081
Bailey, Colin B., ed. (2003). The Age of Watteau, Chardin and Fragonard: Masterpieces of French Genre Painting. Ottawa: National Gallery of Canada. ISBN 9780300099461
—, ed. (2007). Gabriel de Saint-Aubin, 1724-1780. New York: Frick Collection. ISBN 9780300099461