Talk about a tough audience. The task of winning back people like Franklin now falls to the Gap’s new CEO, Paul Pressler, a former Disney exec who ran the Magic Kingdom and other theme parks. Pressler said last week the new job’s a natural fit, since theme parks and retailing have a lot in common. Then again, nobody’s lining up to get into a Gap store like they do for Space Mountain. Longtime Gap chief Mickey Drexler put the company at the forefront of the casual-attire revolution in the ’90s. But the company overexpanded, and moved too far away from classic clothes (exhibit A: vests). Its Old Navy and Banana Republic divisions have struggled, too, leading to falling sales and profits. In May, Drexler announced his resignation.

Pressler, who is more of a brand marketer than a retailer, says he will leave decisions over “the season’s colors” to “the talented people that do that.” But Candace Corlett, partner at the WSL Strategic Retail consulting firm, says the Gap needs a CEO with fashion sense: “Where the Gap comes short–clothing design–is where the new gentleman doesn’t even pretend to have expertise.”

Pressler is holding his cards close to his, er, vest. He said last week that he would spend 60 days working in the stores and learning the business–a nod to all Gap employees, who have to do the same thing when they join the company. He also endorsed the popular notion that the Gap should get back to the classic clothes that made it a retailing giant. In the recent past, he told CNBC, “a lot of the traditional merchandise wasn’t there.” Even if he puts it back on the shelves, he’s got other worries, like the economy and consumer fears about war. Shoppers may keep their wallets in their pockets this fall. The question is, will those pockets be in Gap pants?