Gap's Fashion, Pop-Culture Highs and Lows Through the Years

— -- The announcement by Gap Inc. that it is closing a quarter of its namesake stores in North America by January may bring to mind the retailer's many fashion and pop-culture moments through the years, including some iconic advertising campaigns.

"The brand has struggled a bit more recently finding its place in a new competitive market filled with fast fashion," Morningstar senior equity analyst Bridget Weishaar said, though the company had "moments of success" in 2011 and 2012.

Gap Inc., which owns Banana Republic, Old Navy and other brands, will close 175 stores and cut 250 jobs at its headquarters in San Francisco. The company was founded in 1969 by Don and Doris Fisher, who sold Levi’s jeans and records in its first store.

"As seen from the recent announcement, the day of 1,000-store fleets is a thing of the past," said Simeon Siegel, Nomura Securities executive director, equity research. "Being large comes with its own risks and Gap is working to evolve into the new normal of continuing to drive impressive sales volume while offering product with the sought-after individualism.”

Here's a look at some fashion and pop-culture hits (and maybe some misses) in Gap's history:

1980s and on: Drexler, Denim

After fashion businessman Mickey Drexler was named president of Gap Stores division in December 1983, he expanded upon and complimented the store's denim focus with colorful apparel.

"[Drexler] helped shape the view that we know Gap is today: well-made, good pieces for everyone at a price that didn't cost you an arm and a leg," celebrity fashion stylist Catherine Peridis said.

In the 1990s, Gap famously featured celebrities wearing Gap jeans, including rapper LL Cool J in baggy jeans and a non-Gap FUBU hat in 1999:

Once hugely popular, Gap T-shirts and sweatshirts have lost their cache.

"Whether due to fast fashion, Internet or something greater, today’s consumers want fashion and individuality," said Siegel. "Logos have faded as individualism has grown."

1989, 1996: Turtlenecks

Gap probably can't take sole credit for popularizing the turtleneck in the 1980s and early 1990s, but the company certainly had a presence in the space.

In 1989, Gap's successful "Individuals of Style" ad campaign featured unconventional models, such as writer Joan Didion in 1989 with her late daughter Quintana Roo in black turtlenecks.

Sharon Stone wore a charcoal gray Gap turtleneck to the Oscars in 1996:

Late '90s: Khakis

Gap's most iconic moment was its khakis ad campaign, according to Weishaar.

Peridis agreed, adding that the company's corduroys were also a big hit.

"As a child who grew up in the '80s and '90s, I can still hum the Gap khaki and cords ads," Peridis said, noting a 1999 ad set to the tune of Donovan's "Mellow Yellow," which happened to feature actress Rashida Jones ...

... and James Clarke's "Blow Up a Go-Go" in the same time period:

2004: Sarah Jessica Parker

Gap decided to showcase "Sex and the City" star Sarah Jessica Parker in a few ads to celebrate "the expression of individual style," including its "How Do You Wear It?" campaign for fall 2004. The company went beyond just colorful basics and accessories with shrunken jackets and funky cardigans. The company also produced an ad called "Pretty Khaki."

Though some enjoyed the appearance of glamorous star Parker in Gap ads, critics, including the research firm Fashiobi, said the pairing was a poor match between a simple brand label and its commercial spokesperson.