Meanwhile, Gap’s hurdles are mounting. For the last several years, growth at AthletaOld NavyBanana Republic

What plans Dickson has for the company may be discussed on Thursday when he speaks on Gap’s earnings call. It will be just his third day as CEO, but his ties to the company date back to November when he joined the board. The company is expected to report a third straight drop in revenue.

“Ultimately, Gap’s problem is that it doesn’t have any sales growth,” said Morningstar analyst David Swartz. “At some point, you have to show brand relevance.”

Gap declined to comment for this story. 

Dickson will follow a string of CEOs since the board ousted Drexler in 2002. The company first turned to Paul Pressler — the former head of resorts and theme parks at Disney. Five years later, Glenn Murphy, who had led Canada’s largest drug store chain in a period of solid growth, took over.

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All the turnover in the C-suite has left the company flailing at a variety of strategies. Its recent attempts at buying brands and launching concepts have mostly flopped. In 2021, it sold IntermixKanye West

Dickson, 55, is known for thinking big and not being afraid to shake things up. At the top of that list was a successful overhaul of Barbie that included transforming her look with wider hips and half a dozen skin tones. Investors appear to be counting on that kind of change, with Gap’s shares gaining since the company announced his hiring last month after searching for a year.

During two separate stints at Mattel, Dickson used audacious marketing to generate buzz around Barbie, but the sales gains often didn’t last. To boost the doll’s profile, he had strategies such as enlisting Vera Wang to create looks and convincing Mattel to spend a reported $30 million on a six-story Barbie store in Shanghai with its own karaoke bar and beauty salon.

All the publicity paid off as Barbie sales rebounded. FreshJones ApparelNine West

Retail experience

At Jones, Dickson, who worked at Bloomingdales and Estee Lauder

A few months later in May 2014, Dickson returned to Mattel, but this time as chief brands officer. Sales for Barbie and Mattel were mostly stagnant or declining until big gains during the pandemic. Over the course of Dickson’s second tenure with the toymaker, the shares fell by about 40%.

After a marketing blitz, including turning a Southern California mansion into a Barbie Dreamhouse, the Barbie movie had the biggest opening weekend of any film this year. It has since grossed more than $1 billion globally and pushed the brand into the zeitgeist, but it remains to be seen how much the movie will boost Mattel’s sales. The toymaker reiterated in July that it expected revenue to be flat this year, although the company expects Barbie to grow.

A concern beyond whether Dickson’s ambitious strategies have staying power is that they might get held back by the Fisher family, which founded Gap in 1969. William Fisher, the son of the founders, is on Gap’s board and the family remains one of the largest shareholders.

“The place has been a revolving door of executives,” Swartz said. “The problem ultimately is the Fisher family. They bring people in and don’t give them a chance to do what they need to do.”

Other analysts are optimistic, though. Dickson’s “strong combined history of brand reinvigoration and prior apparel experience comes at an opportune time for Gap,” Goldman Sachs

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“The company is not in any danger of financial distress,” Swartz of Morningstar said. “I don’t think it’s impossible to fix.”