If you were a kid anytime in the past century, you probably owned a pair of Keds. The ubiquitous canvas sneakers are undergoing their latest makeover in an effort to build buzz among a different constituency — 20-somethings.

To do that, a 32-foot trailer designed to look like a shoebox is hitting the road for stops at U.S. college campuses. The “How Do You Do?” campaign invites students to design their own shoes at a touch-screen kiosk and purchase them. Each stop will feature shoes inspired by that city — for example, the March stops in Austin, Texas feature shoes in denim, chambray and twill with Western details.

“As people go through identity crises, so do the brands,” Kristin Kohler Burrows, president of Keds Group told The New York Times. She said one of the goals of the campaign is to “awaken people to the fact that [Keds] is an iconic brand.”

Keds were first introduced in 1916. By 1930, the company had unveiled a line of high-heeled shoes — dubbed “Kedettes” — in an effort to appeal to women. The shoes have adorned the feet of Marilyn Monroe, Jackie Kennedy and Katherine Hepburn.

And this wouldn’t be the first time that Keds have been a trend among young people. In the 1980s and 1990s, they had a place in the closets of many teenage girls, alongside babydoll dresses, slouch socks and lace-trimmed bike shorts. Keds also tried to attract a similar audience in the mid-2000s, when actress Mischa Barton — then starring on young adult-centric mega-hit The O.C. — became the shoes’ spokesperson.

Now the company is trying to appeal to the millennial demographic by featuring artists and young people giving back to their communities in its ads. Keds is also running a design contest, and adopting a campaign Twitter hashtag. “We really feel that what’s important to this consumer is to engage with a brand” and experience it firsthand, Kohler told the Times.

Maintaining the “cool” factor of any product is a tricky proposition. In a past Knowledge at Wharton story, marketing professor Jonah Berger noted that fashion is fertile ground for fads because clothing is a way to communicate something about a person’s identity and style. “Styles often start with one group, and then another group starts to use it because they want to look like that first group,” Berger said. But when that second segment adopts the trend, “the meaning may be lost.”

He and other faculty said it is critical for brands to understand the potential value of a product before pouring money into keeping it current. The Times story reported that Keds spent $1.68 million on advertising from January to September of last year, compared to $450,000 during that same time in 2009. “You should only invest in things where you can do a credible job of forecasting that the perceived value of your offering compared to your competition will be sustainable,” Wharton marketing professor Leonard Lodish told Knowledge at Wharton. “You need to understand the factors that will make that happen.”