Like many stores at the mall, Gap (NYSE: GPS) has been struggling to recapture its past glories.

During the 1980s and 1990s, the brand was hip, hot, and in heavy demand. But in recent years, that demand has cooled, leaving the retailer looking for ways to connect not only with younger customers, but also to bring back the older ones who made the company cool in their youth.

To do that, the chain has literally gone back to its roots, releasing a limited-edition clothing collection called the '90's Archive Re-Issue. With items for both men and women, the line features "iconic styles from the '90's including the Bodysuit, Reverse Fit and Easy Fit Denim, Pleated Khakis and the timeless Pocket Tee," according to a press release. The collection goes on sale online and in select stores nationally Tuesday.

What is Gap doing?

The company is seeking to recreate some of its '90s magic. In addition to the actual retro clothes, the company worked with director Kevin Calero to create Generation Gap, a film that is a "contemporary homage to the iconic Gap ads of the '90's with references to 'Mellow Yellow,' 'Crazy Little Thing Called Love' and 'Just Can't Get Enough' and updated with a modern twist." It's basically an effort by the struggling chain to remind people of the time when they liked Gap and the company was a taste-maker.

"The '90's is having a sartorial moment and we have an archive of pieces that set the tone for that decade commercially and culturally, so it seemed right to reissue some of those pieces and the stories that come with them," said Chief Marketing Officer Craig Brommers. "Generation Gap came together in a celebration of who was with us then and who we are with now -- it has, at its heart, that simple truth that we can take from the past but also celebrate our future."

Will this work?

It's hard to picture millennial shoppers becoming enthralled with this particular retro look, but the collection/movie/ad campaign may remind their parents that the chain exists. It's easy to see what Gap is trying to do in creating a connection to its more successful days, but there is also risk involved.

These efforts might reinvigorate Gap by reminding lapsed customers why they used to shop there. It could also come off like an old guy retelling the tales of his high school football glory days long past the point anyone wants to hear them.

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Daniel Kline has no position in any stocks mentioned.

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