Microcars have always been cheeky novelties, bubbly one- or two-seaters with toy-like motors and style from The Jetsons, reserved only for the dusty garages of avid vintage collectors that appreciate them—and never drive them. But recently, these miniscule cars from the post-WWII era have been setting the foundation for a new wave of carmakers, who see microcars as the picture-perfect future of urban transportation.

In theory, microcars have it all: they’re refreshingly cheap, perfect for navigating through urban traffic, and small enough to squeeze into tight parking spots. With cities projected to house 66% of the world’s population by 2050, the ride’s got the makings of a dream car on paper. But microcars have never fared well in America, where bigger is actually often better, and extra layers of sheet metal and tall seating positions bolster the illusion of security—even if auto insurance rates back up modern microcar safety claims.

Jim Janecek, who’s been involved with the Vintage Microcar Club for over two decades, calls the crest and troughs of microcar interest a pipe dream. To Janecek, America’s “aversion to microcars” will be no different this time around. The Smart Fortwo, one of the more successfully regarded modern microcars, experienced a surge in sales when it first launched in 2008, but has faltered since, even in European countries where they’re more culturally accepted.

“People think, ‘Small cars are just what America needs! They’re good on gas, cheap, and you can park it anywhere!’ That’s been a thing that sticks with people for years and years,” Janecek says, attributing initial Smart sales to its novelty factor. “If there was a viable market in the U.S., the Smart would have filled that gap.”

It’s a good point. According to global consulting firm Frost & Sullivan, more than 35 microcars have been debuted at auto shows up to 2013, with few moving past the concept stage. For these toy-like oddities seeking to be once again part of America’s mainstream driving culture, is a microcar of the past an ill portent?

Automakers are surprisingly resilient, despite the roster of failures: Th!nk City, Corbin Motors, and G-Wiz REVA among others. Numerous independent automakers have joined the ranks of industry giants trying their hand at reinventing the hot wheels. This time, they’re determined to get it right: tucking in electric motors, experimenting with driverless concepts, and tipping hats to the original vintage microcars by incorporating nostalgic elements in exterior design—all to capture the affinity of millennials.

“Millennials have the ability to change the game when it comes to being early adopters,” says Roman Kuropas, CEO of Innova EV, which is testing fleets of its all-electric, two-seater “Dash” microcar on college campuses. They’re already well acquainted with ride-sharing apps, and genuinely interested in sustainability and alternative mobility themes, including adopting cars equipped with Internet-of-Things connectivity as the ultimate gadget. According to a 2014 Deloitte study, 59% of Gen-Y consumers see themselves driving an alternative engine in five years. To many like Innova EV, “the most important demographic” seems to get the intellectual allure of microcar-led transportation.

Still, no matter what safety features are built in—Smart’s “reinforced high-strength steel tridion safety cell” engineered to distribute energy from a crash, for example—perception with size has always been a problem.

“When people see a microcar, the first thing they think is ‘Oh, I don’t want to get hit in that,’” says Jerome Vassallo, VP of Sales at Elio Motors, “even though there are Formula One racecars going around the track at 200mph, and we all see them crash and get out fine.” Elio plans to produce a three-wheeled commuter vehicle in late 2016.

To address the persisting perception problems tied with size, auto designers are trying to use aesthetics. On one hand, it’s about communicating safety and legitimacy; on the other, it’s about redefining what’s cool altogether.

“A lot of professional car designers will tell you that the first battle you have to win with a customer is one of desire,” says Paul Snyder, who is the chair of transportation design at the College for Creative Studies. Whereas the microcars of the past thrived on being the sole affordable choice for war-worn wallets, consumers today can choose, meaning the creature comforts of modern microcars must override the incentives of any bigger, faster, and “better” alternative.

Jason Hill, founder of eco-friendly transportation design firm Eleven LLC and a teacher at the ArtCenter College of Design, believes there’s a scarcity of successful small cars that visually project the aura of safety. “It has to be cute and friendly, but not goofy. It has to look intelligent enough to get you places,” Hill says. “Companies have a responsibility to pull customers ahead into the fresh and tomorrow, but also meet expectations.”

Therein lies the challenge for auto designers: making a microcar which is “short, narrow, and tall” into something sexy, a term usually reserved for cars that are “low, wide, and long.” Snyder says there are clear styling trends in the industry—most notably, Audi’s Bauhaus styling and BMW’s body-contouring “flame surfacing”—but that a resurgence of nostalgic themes has been coming back into play. Like the classic Volkswagen Beetle’s romantic 2015 re-edition, or less overt cues like the latest Bentley’s running boards from the ‘30s, microcar designers are experimenting with nostalgic styling, and incorporating successful elements of their vintage counterparts—but not so that “retro-heritage design becomes a one-way dead end,” Hill says.

Gabe Chan, who got into car culture working at his uncle’s repair shop in San Francisco, doesn’t think designers have nailed the look yet. “Cars are trying to be sporty-looking and aero right now, but microcars essentially look like a box,” the 21-year-old says. Nobuto Kato, 23, who grew up in Tokyo’s saturated car culture, is a little less apologetic. “The design is way ugly and unpractical,” he says.

Hill estimates it will take at least a generation and a half before the perception gap is closed. “It needs to be executed well,” Hill says, reflecting on insights working on the Aptera Typ-1, a high-efficiency three-wheeler that ultimately failed, and the success of the MCC Ecosprinter, which became the basis for the Smart. “So far, it’s the same story done in the same way. It’s wildly predictable and naïve.”

But like most mobility futurists, he remains optimistic modern microcars will eventually make it out onto city roads, in what many predict will be a multi-tiered transportation society with various vehicles for specific purposes, in place of the one-car-fits-all model today.

“Microcars are there, they’re coming…it’s just about closing the gap,” Hill says.

The biggest format change in play? Automation. Few people are interested in owning a cutesy microcar, but hopping in one for a quick ride to the airport—especially when self-piloted cars are new and novel—may reset the status and perception level. If the highways of two decades from now are filled primarily with tiny, packetized robot cars, privately owned microcars might not just be tolerated—they may be preferred.