In the mid-1970s, Drexler was a
merchandising vice-president at
Abraham & Straus in
Brooklyn, New York. He has also worked at
Ann Taylor,
Bloomingdale's, and
Macy's. He was on
Apple Inc’s board of directors from 1999 until 2015.
Gap Inc. Drexler is often credited with Gap's meteoric rise during the 1990s. Prior to his involvement, Gap had been a relatively small chain selling private and public
brands. Under Drexler the company made a dramatic shift to
private label brand merchandise and expanded rapidly to become an iconic part of
1990s pop culture, such as "khakis, basics and casual Fridays". Television advertisements featuring songs such as "Mellow Yellow" and "Dress You Up in My Love" showcased the relaxed American casual look that defined the Gap brand. During his time at Gap Inc. he had worked alongside
Steve Jobs, who was a board member of Gap Inc. at the time and a friend of Drexler. On May 22, 2002, however due to a sales slump and ballooning debt, plus his management style which clashed with the Fisher family, Drexler was abruptly forced to announce his retirement by Gap founder
Donald Fisher. Drexler stayed on as CEO until September 26, 2002, when
Paul Pressler was named as his successor. Drexler was bitter about his ouster but it was validated when sales rebounded one month after his departure.
J.Crew Group The J.Crew Group, an American clothing and accessories retailer based in
New York City, was founded in 1983 with the launch of its
catalog and expanded into
brick-and-mortar retailing in 1989 with its first store at the
South Street Seaport in New York City. J.Crew hired Drexler as chairman and CEO in 2003 after his abrupt departure from Gap. Applying similar strategies from Gap, Drexler sought to reposition the J.Crew brand as a truly upscale boutique. What was once a low-priced, American, dressy-casual brand became more an upscale, dressy-vintage American brand with "frills included". Drexler noted that "J.Crew raised prices and underwent expansion during years when consumers became more and more thrifty". On January 18, 2019, Drexler announced his retirement as chairman, but will remain a strategic advisor to the Office of the CEO and the board. ==In popular culture==