Gap Is Doing Everything It Can to Become Cool Again With consumers embracing cheaper fast-fashion alternatives like H&M and Zara, the retailer has found itself in need of a makeover.

Gap was once so cool that Sharon Stone wore one of its turtlenecks to the Oscars.

But as consumers turned to cheaper fast-fashion alternatives, Gap failed to catch up. In the age of Instagram and instant fashion, the retailer's designs feel dated.

Now, America's largest apparel retailer is embarking on a turnaround plan to recapture cool customers by reinventing its supply chain to compete with brands like H&M, Zara, and Forever 21. It's also overhauled marketing and made key hires.

Faster supply chain

Getting faster is a core tenet of Gap's plan.

The risk of trying to predict fashion trends a year in advance is also weighing on the success of retailers such as Abercrombie & Fitch, Ann Taylor, American Eagle, and others, according to Goldman Sachs.

If these retailers have a "fashion miss," it means markdowns, which hurts profits.

Gap is trying to get out of "misses" faster now.

"So what I mean by rebuilt it is we put multiple lanes in our product pipeline. It's got our seasonal lane, but we now have a really good responsive lane. And we have the ability to get back into what's working quicker and get out of what's not working faster," Gap President Jeff Kirwan said at an Investor's Conference this year.

"So the story on supply chain is, as we've been telling it that we're continuing to push on it on a number of the elements, on platform fabric which enables us to get back into season very quickly on some of the test and respond that we've been doing," Gap CEO Art Peck said during an earnings call earlier this year.

A $35 pair of pants called "pixies" at Gap-owned Old Navy shows how the company is adapting to the fast fashion market.

"Old Navy's pixies are the result of a new, quicker, and more flexible manufacturing model," reports Phil Wahba at Fortune. "The brand rolls out pieces in small batches to test demand before mass-producing them, works more closely than ever with suppliers, and accommodates new trends by keeping a stockpile of fabric on hand."

This quick strategy might be why Old Navy is swiftly outpacing Gap. In 2014, the brand amassed $6.2 billion in revenue, making it the third biggest apparel company.

"Old Navy is farthest ahead in realizing this with the changes that have taken place, obviously and the challenges in the business at Gap, changes in leadership, challenges in the business. Those two businesses lag. Banana is probably in the middle and Gap is farthest behind," Peck said in an earnings call earlier this year.

Adapting for the digital age

Fortunately, a bright spot for the brand is its digital branch.

Fast Company reported in April that Peck is trying to focus on mobile shopping experiences, although the site reports he recognizes there are challenges in this.

"I would like to be able to articulate a nice linear path as to what our stores are going to evolve to," he told Danielle Sacks at Fast Company, "But I think it's going to be a lot messier than that."

Connecting with technology is crucial for the company to attract young customers.

"When it was the '70s, gosh, it was the go-to-place, The Gap, [but if you talk to millennials] they look at it as, yeah, maybe it's where you buy stuff for your kids," said Kevin Meany, CEO of consulting firm BFG.

Key hires to become cool again

Back in the day (the Oscars moment was in 1996), Gap was very cool — in part, because of its basics.

"They elevated incredible basics to not just an iconic status in terms of clothing, but also a spirit — you felt like there was such a strong attitude, so much energy," Jessica Navas, chief planning officer of Erwin Penland told Business Insider.

The brand has recently acknowledged mistakes like not offering enough colors, or making merchandise that was too trendy.

Earlier this year, Peck began to solve this problem by replacing creative director Rebekka Bay.

She was known for her fashion forwardness and experience with H&M — but she might have been a bit too much for Gap's discerning customers.

He then made a series of key hires to help revive the brand.

Gap brought on Wendi Goldman of the controversial brand C. Wonder (and formerly of the Gap's own Banana Republic) in February to Gap's executive vice president of product and development — a first for the brand, Fast Company notes.

Gap also hired Steven Sare from Japanese powerhouse Uniqlo to be senior vice president of global marketing and Alessandra Brunialti as vice president of women's designs.

Becoming a marketing powerhouse

But can this new team capture fickle audiences?

That requires advertising — a sector where Gap has struggled recently.

Gap has recently launched a new ad campaign for the fall, which was relatively simple compared to its recent series of misfires, including 2014's "dress normal" campaign, which resulted in several months of declining sales.

Gap has attempted to get in the social media game with a campaign on widely used dating app Tinder.

Meanwhile, Instagram and other social media outlets have played a big part in Gap's demise, the New York Times reports, making Gap feel "dated."

All of this likely frustrating, since at a time, Gap was known for its cutting-edge campaigns and commercials, many of which featured celebrities.

In the company's heyday, it ran a series of ads showing vintage photographs of Ernest Hemingway, James Dean, and Zsa Zsa Gabor wearing khakis, implying that artists and creatives wore its pants. Television commercials like the iconic Khaki Swing ad resonated with customers. This is not the case anymore.

"That's all ancient history," Meany said to Business Insider. "It's what they read about, not what they're experiencing, and to them — Forever 21 & H &M are more meaningful to them, and probably resonate a lot better with their world and who they are."

The next generation

Gap might just be experiencing growing pains.

"[It's] very hard to migrate into the next generation," Meany said to Business Insider. "When I look at that, it's almost like they're in this awkward stage of development as a brand. They're too old to be the new innovative brand they were, but they're too new to be the vintage comeback brand."

In May, Peck seemed optimistic about Gap's outlook.

"I'm pretty encouraged by what I see going forward," he said in the earnings call.

Three months later, it's unclear if Gap can regain its identity.

But the company is aiming to see changes come 2016.

"So the foundation is built, and now we're just operationalizing it and trying to create more value as time goes on. And the full power of the product pipeline is going to evolve over time. And I think we'll see it really starting to show up in 2016," Kirwan said at an Investor's Conference this year.

When Gap reports earnings August 20, we'll see if the brand succeeds at making progress toward being the cool retailer it once was.