Mickey Drexler, the former CEO of Gap Inc. and J. Crew, known as the “Merchant Prince,” discusses his journey from humble beginnings in the Bronx to reshaping the American fashion landscape. He is credited with revolutionizing office attire, launching successful brands like Old Navy and J. Crew, and making khakis cool. Drexler’s approach to fashion is rooted in emotion and simplicity, with a focus on timeless, elevated basics.
After leading Gap to unprecedented success, Drexler was fired in 2002 but refused to sign his severance package to avoid a non-compete clause. Undeterred, he invested in J. Crew and launched Madewell, demonstrating his resilience as a serial entrepreneur. Known for his candid communication style and hands-on leadership, Drexler continues to innovate in the industry, co-founding the brand Alex Mill with his son and designer Somsack Sikhounmuong.
Despite his successes, Drexler remains grounded and emphasizes the importance of staying curious and learning from mistakes. His unorthodox approach to retail, including minimal discounting and a focus on customer experience, sets him apart in a fast-paced industry. Drexler’s refusal to conform to traditional investor expectations allows him greater freedom and control over his businesses, maintaining a long-term vision for sustainable growth.
Reflecting on his interactions with Steve Jobs and lessons learned from being fired from Gap, Drexler shares insights on entrepreneurship and the importance of pushing boundaries. His commitment to authenticity and integrity in retail, as well as his willingness to adapt to changing trends, have solidified his place as an industry icon. As he approaches his 80th birthday, Drexler continues to exemplify the spirit of innovation and resilience that defines his storied career.
