The affable Yorkshireman, son of a carpenter and a window-dresser for the British department store Marks & Spencer, graduated from the Royal College of Art in 1994. After a stint in New York working for Donna Karan, he moved to Milan to work for Tom Ford at Gucci, the job he had when, in 2001, he met Rose Marie Bravo, then the American chief executive of Burberry. Within weeks of that initial meeting, she hired him to replace the designer Roberto Menichetti as Burberry’s creative director. As Burberry’s creative chief, working first alongside its chief executive officers Ms. Bravo and then Angela Ahrendts, Mr. Bailey came to enjoy a run as the golden boy of British fashion. In 2013, Ms. Ahrendts took a job at Apple as head of retail, and less than a year later Mr. Bailey — already in charge of an enormous portfolio that ranged from overseeing 50 collections per year to store design and marketing — was given his greatest challenge to date: becoming her replacement, and the new chief executive. After three rocky years during which Mr. Bailey juggled both his creative and management responsibilities, Marco Gobbetti of Céline was tapped to become Burberry’s new chief executive, with Mr. Bailey relinquishing the role to take up a newly created position as Burberry president in July 2017. Then, on the last day of October, news broke that Mr. Bailey had something of a change of heart. His last collection for Burberry would take place during London Fashion Week, on Feb. 17 2018.