That community gelled in 2006, when the Cool Kids played DJ duo Flosstradamus’ monthly party at Town Hall Pub. The indie-rock crowd and hip-hop heads loved the Cool Kids, who had only three songs to their name. Josh Young of Flosstradamus introduced the Kids to Diplo, who will release Totally Flossed Out—a mix-tape of original Cool Kids tracks (mixed by Flosstradamus)—this summer on his label, Mad Decent. Another Town Hall guest, DJ A-Trak (Kanye West’s touring DJ), recruited the rappers to his start-up label, Fool’s Gold. It wasn’t old-school references that grabbed A-Trak. “When I heard ‘88,’ that’s when I really got into it,” he says. “I liked that they weren’t just on some throwback shit, because the rhyming still sounded really current.” By summer’s end, that relationship will yield two Cool Kids 12-inches, packaged together for iTunes.

Relaxing in his cool West Loop condo on a hot June afternoon, Ingersoll streamed track after track of unreleased material (he and Reed have stockpiled nearly a full album of finished songs) proving that the duo is vastly more diverse than it’s shown the world so far. “A-Trak understands that we don’t want to be the hipster-craze group—we have real shit to get off our chests,” Ingersoll says. “We check all the little message boards, and they’re all like, Hey! It’s the happy-go-lucky party rappers! They don’t talk about shit! We got a song called ‘Running Again,’ where [Mikey] talks about dying and being in a car crash. It’s gonna fuck people up.”

These days, the Cool Kids are at home with raucous parties and young retro street-wear fashion zealots. The look isn’t just integral to the show—it informs the tunes. Reed and Ingersoll rap about totems of cool: limited-edition sneakers, edgy graphic T-shirt lines and pimped-out BMX bikes. Held up against mainstream hip-hop materialism (like Kanye West’s tributes to Louis Vuitton), Cool Kids’ fascination with trends is a function of modest cash flow (Reed is a mere 19; Ingersoll is 24). And there’s a boy-from-around-the-block innocence to that braggadocio when Reed raps about coaxing a pretty girl to ride his bike pegs on “Black Mags.”

Still, it’s Ingersoll’s no-sample approach that’s the group’s signature. Working from a palette of analog synth and found sounds, he’s known to cannibalize his original beat structures and the group’s vocals, as on “Whatup Man,” which has a rhythm constructed from the clank of a cowbell and onomatopoeias of clap and pop. “I just don’t sample because we can’t afford it,” Ingersoll says. His measured flow and goofy but astute wordplay (“We’re the gold-chain backpackers,” he raps on “Pop”) round out Reed’s more acidic rants. At the end of the day, these stylists are more about good vibes than anything. “Yesterday someone left me a [MySpace] comment like, ‘Yo. You make me comfortable being myself and that’s dope,’?” Ingersoll says. “I responded to that one. That shit’s dope. I didn’t even know what the fuck a hipster was till this year.”

The Cool Kids play We (Heart) Chicago on Friday 13, at A.Okay Official Saturday 14 and Pitchfork Music Festival on Sunday 15.