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Fading Out of Fashion

Gap, once the king of casual cool and now struggling to define itself, is reported to be considering going up for sale.
Gap, once the king of casual cool and now struggling to define itself, is reported to be considering going up for sale. (By Justin Sullivan -- Getty Images)

"We know it will take several seasons of compelling messaging and product to rebuild our traffic," chief executive Paul S. Pressler said.

The company has reinvented itself before. Gap, whose name references the "generation gap," was founded in 1969 in San Francisco, where it is headquartered. It started out selling Levi's jeans, but under the leadership of legendary chief executive Millard "Mickey" Drexler expanded its merchandise to include basics that were fashionably easy to throw together.

Drexler turned Gap into a powerhouse. He was known for his hands-on approach, even picking colors for polo shirts. In the mid-1990s, when the brand began to falter from overexposure, Drexler introduced Old Navy, which initially succeeded in providing affordable fashions for the entire family. A quirky 1998 TV spot featuring young adults dancing madly to Louis Prima's classic "Jump, Jive An' Wail" while wearing Gap khakis quickly became a hit.

But sales soured a few years later as the chain courted fickle teenagers, turning off older, more loyal shoppers. By 2002, Drexler resigned and Pressler replaced him.

"As they've gone back and forth between being fashion-forward and being basic, they've really confused their customer," said Christine Chen, an analyst with Pacific Growth Equities and who owns shares in the company.

Pressler, who was hired from Walt Disney Co., had no experience running a retail chain. In an early coup under his leadership, Gap signed Madonna and rapper Missy Elliott to model corduroy pants for fall 2003. That helped update an image that often walks the line between classic and boring.

However, Pressler's greatest impact arguably has been in the back office, where he improved inventory management and began tailoring stores to different kinds of customers. But that hasn't been enough to compete against retailers who sell a lifestyle as much as they do apparel.

Pacific Sunwear and Abercrombie & Fitch, which owns Hollister, blare music inside their heavily themed stores. Hollister stores look like surf shops. Abercrombie once hired male models to stand shirtless in front of its stores.

Pamela Burns, a personal shopper in the District, said she has all but given up on Gap. She used to find cute flannel pajamas and expensive-looking velvet blazers there. Now, she said, she walks out almost as soon as she walks in.

Even the basics have lost their appeal. This holiday season all she bought at Gap was a candle.

"I feel like there's no style right now," she said. "Who wants to really walk in for khakis and white shirts?"

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