Founded in the late ‘60s by San Francisco real estate developer Donald Fisher, Gap was initially meant to be a place for California hippies to buy jeans. Fisher’s initial vision for the store was closer to American Apparel or Urban Outfitters than Gap we know today. Fisher toyed with the name “Pants and Discs” for his store that would sell denim and records to his hip, young customers. Fortunately, he eventually landed on “The Gap.”

Fisher’s store was a hit. Gap struggled to keep their signature Levi’s in stock and quickly began merchandising its own brand of jeans. In the early ‘70s, Gap added T-shirts and sweats in numerous colors to compliment their denim, cementing their reputation as the coolest place to buy the basics. 10 years after opening, there were 400 Gap stores in America, and the chain was barreling toward a half-billion dollars in annual sales.

By the ‘80s, Gap’s loyal young customers were growing up, and Gap decided to grow up with them. A major move for the store hit in 1983, Millard “Micky” Drexler (probably better known to modern shoppers as the former chairman and CEO of J.Crew Group) was named President of Gap Inc. Drexler wanted Gap to create a business casual, cool look for their customers as they became career men and women. Drexler saw that selling jeans and other basics would limit growth; the time had come to sell a lifestyle.

Gap would become the destination for the aspirational, emerging upper middle class. This meant overhauling inventory to include khakis and dress shirts, repainting the colorful walls to a soft white, and creating the iconic, spare, modern look we still associate with Gap stores today. Every aspect of Gap’s identity was overhauled, down the regimented music playlist. Within six months, 450 Gap stores had been made over. Now Drexler and company needed to take their plan national with an ad campaign to match their in-store strategy.

The opening salvo in Gap’s advertising rebrand was 1988’s “Individuals of Style” campaign. The classy black and white print ads shot by Annie Leibowitz featured NPR approved cultural luminaries like Joan Didion, Spike Lee, and Whoopi Goldberg sporting the new line of Gap basics.

They followed this campaign with the aesthetically similar "Who Wore Khakis”" campaign in 1993, again featuring black and white photos. This time, the ads featured historical figures like Amelia Earhart and Miles Davis wearing khakis.

Both campaigns clearly established Gap’s utilitarian vision of upper middle-class fashion—and the idea that the clean simplicity of that style has manifested itself across several eras while proving that it can (and should) be available to all walks of life. “Individuals of Style” presented the target audience with approved cultural figures that someone with a media diet of broadcast TV probably wouldn’t recognize. “Who Wore Khakis” leveraged the educational barrier between the desired Gap customer and a shopper at a traditional department store or Wal-Mart. A less educated consumer would look at these ads and think “Who are those people in the pictures?” The college educated target audience would feel like they were “in the know,” being spoken to directly. Either way, both groups can comprehend the ads on some—albeit likely different—levels. The takeaway? Gap’s vision of style wasn’t just classy, it was classic

After these successful print ads came two commercial campaigns that are forever seared into the subconscious of any Generation X-er or Millennial whose parents owned a TV: “Khakis” and “Everybody In.” The commercials were stripped down music videos featuring attractive young people dressed almost identically, singing and/or dancing along to songs from various genres. With the diversity of the songs and cast, coupled with the clean uniformity of the clothes and sets, these videos were tailor-made for the NPR/Starbucks crowd—without alienating any demographic. Impressively, at a time where the world was suddenly getting smaller and more connected, they made that human-to-human connectivity...frankly, cool. They champion diversity, but present that diversity in a sanitized, modernist environment. And of course, every actor, singer and dancer is dressed almost identically.

The brand was established: every upwardly mobile young professional, every thoughtful cool guy and every shopper seeking great basics needed a pair of Gap khakis (not to mention its lineup of jeans, tees and other apparel). This wasn’t just an era of cultural saturation for Gap, this was also an era of retail dominance. This Gap decade was bookmarked by a sales jump of 30 percent from 1991 to 1992 and 39% growth in 1999.

Growth continued at a rate in the double digits year by year until 2002 when the stock prices plummeted from $50 to $8. Drexler was let go, but the bottom continued to fall out. A quick succession of executives saw Gap’s value drop lower and lower. In 2006, the retail giant posted a 1.5 percent loss, and in 2009, the company took a nearly 8 percent hit. These losses were felt across Gap’s empire. In 2005, shares of Gap Inc. (which includes Banana Republic and Old Navy) fell a massive 16 percent.

Gap’s downfall was as meteoric as its rise, and the reasons for the store’s failure weren’t far off of the secret to the store’s initial success. In the ‘90s, retail manufacturing and supply chains weren’t sophisticated enough to bring runway looks to the masses. Designer looks were reserved for those who could pay for them. Gap filled a need by offering another way to convey status: basic, yet fashion-forward looks at a mall-friendly price point. It wasn’t as impressive as something like Chanel, but you knew it was Gap just by looking at it.

By the mid-2000s, stores like H&M, Zara and Forever 21 perfected methods of delivering “fast fashion” that aped runway looks at a fraction of the price. The desire to feel fashionable while your clothes remained affordable was being met better and cheaper almost everywhere else in the mall outside of the airy confines of Gap. As retail analyst Candace Corlett told Racked, “The consumer has made room in their closet for fast fashion…How many tan khakis and white button-down shirts does someone need?”

At the same time, stores like Uniqlo (which arrived in the US in 2005) were doing what Gap had always done, but better. Uniqlo could deliver essentials like jeans, dress shirts, and vests well under Gap’s price point and in styles that millennials found more appealing. Gap was suddenly fighting a battle on two fronts: they lost both the battle of the bottom line and the culture war. All of a sudden, Gap was both too expensive and not cool enough.

Nowhere is this shift more evident than in comparison to Old Navy. Gap’s lower-end sister brand began as a Gap outlet store, but has fared much better in recent years. After stumbling alongside Gap for much of the 2000s, the store has shifted to compete with fast fashion stores. As a result, their bottom line and media buzz remain healthy. As analysts see it, Old Navy is keeping Gap afloat. Neither Gap nor their higher-end store Banana Republic have been able to reinvigorate their brand, despite the efforts of numerous executive regimes.

After about a fifteen year reign, the “gap” that Gap initially inserted itself into no longer exists. The barrier between the department store and the runway had been demolished, and the young emerging professional class prefer a cycle of hip, new looks to brand name khakis.

Gap was the perfect representation of a particular time and place. As the ‘90s embodied an era of upward mobility, positive social politics, and a championing post-’60s (but pre-internet) human connectivity, Gap represented the progressive idea that every person could stand on the same level of style—albeit with the brand’s selection of quality basics, naturally. With fast fashion exporting the runway into the closets of millions, and the push to define individual personal style more pronounced than ever, Gap was simply outmoded by the turn of the 21st Century. The ‘90s are over. So is Gap.