Bailey wrote and edited the book Tham ma da: The Adventurous Interiors of Paola Navone, which was published by Pointed Leaf Press in 2016. He has interviewed hundreds of leading architects, artists, designers, and others, including David Adjaye, Tadao Ando, Thom Browne, Zaha Hadid, Jacques Herzog, Ian Schrager, and Kanye West. At Surface, Bailey helped launch the Design Dialogues live conversation series, of which he was a frequent moderator, and the creative agency Surface Studios. During three years of reporting for The New York Times Magazine, from 2011 to 2014, he interviewed authors, celebrities, politicians, and cultural figures such as Al Sharpton, Tony Hawk, Rodney King, and Cyndi Lauper for a “How To ...” column.
Bailey is a trustee of the Noguchi Museum in Queens, New York. He also serves on the New York honorary committee of the L’Ecole jewelry-making school, which is supported by Van Cleef & Arpels. He has been on the juries of the CFDA Fashion Awards, the James Beard Restaurant Design Awards, the Rado Star Prize, and the Swarovski Designers of the Future Award.
Born and raised in Denver, Colorado, he is a graduate of Columbia University’s Graduate School of Journalism and Dickinson College in Carlisle, Pennsylvania.