In a director/PDMR (person discharging managerial responsibilities) document Burberry filed with the London Stock Exchange, it was disclosed that Bailey will be cashing in his shares in Burberry for £16m.
Bailey, who has been with Burberry for 17 years, has been chief executive of the company from 2014 until last year, when Marco Gobbetti took the helm. Bailey retained creative control.
The change in management took place amid a 10% profit drop last year. This disappointing financial performance led Bailey to take a 75% pay drop to £1.9m.
Under Gobetti, the brand has reported "better than expected" first-quarter sales in July this year. Burberry's like-for-like sales grew by 4%, twice the rate of growth forecast by analysts.
Burberry has not responded to a request for comment.