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Mickey Drexler, the former CEO of Gap Inc. and J. Crew, is still in start-up mode as he approaches his 80th birthday. Known as the “Merchant Prince,” Drexler has had a significant impact on the fashion industry, changing the way Americans dress with his work at Gap and J. Crew. Despite his success, Drexler’s upbringing in a one-bedroom apartment in the Bronx shaped his entrepreneurial spirit as he dreamt of making moves to escape his reality.

Drexler’s career has been marked by success and setbacks, from taking Gap from a $400 million business to $15 billion, to being fired in 2002 after a slowdown in sales. Refusing to sign his severance package, Drexler immediately invested in J. Crew and continued to make waves in the industry. Known for his unconventional leadership style, including using the office intercom as a megaphone, Drexler’s achievements are a testament to his determination and vision.

Now, as the co-founder of Alex Mill alongside his son and designer Somsack Sikhounmuong, Drexler is once again in start-up mode with a brand focused on elevated basics for men and women. Rejecting the trend-driven nature of streetwear, Alex Mill offers a more timeless approach to fashion. Despite his age, Drexler remains actively involved in the retail business and is focused on expanding the brand, with a vision to leave behind a healthy economic company.

Drexler’s legacy includes his famous clash with Steve Jobs over the design of the first Apple Store, showcasing his willingness to speak his mind even to the smartest person in the room. Reflecting on his mistakes and lessons learned, Drexler emphasizes the importance of staying curious and continually evolving in order to succeed in the constantly changing retail industry. His dedication to retail and refusal to compromise on his vision set him apart in an industry known for constant change and competition.

As he approaches his milestone birthday, Drexler shows no signs of slowing down, with plans to expand Alex Mill and continue his entrepreneurial journey. With a focus on authenticity and a commitment to providing value to customers, Drexler’s approach to retail offers a refreshing alternative to the constant discounting seen in the industry. Despite his unconventional path and refusal to conform to industry norms, Drexler’s impact on the fashion industry is undeniable, earning him the title of an icon in the world of retail.

In a world where Gen Z throws around the word “iconic” for everything from Netflix series to smoothies, Mickey Drexler has earned the title through his enduring influence on the way Americans dress and his innovative approach to retail. As he looks towards the future, Drexler continues to embrace his entrepreneurial spirit, paving the way for the next generation of retail leaders with his unconventional leadership style and commitment to authenticity in an industry known for constant change and competition.

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