ShowYouSuck at Jugrnaut. "You can walk into Jugrnaut and see me and St. Millie or other artists. Since they're open all day, artists like me who don't have a day jobs, that's where we hang out." Credit: Ryan Lowry

Chicago hates you. That’s the message many local rappers face when they come up in the Chi, which has also come to be called “haterville” and “the city of hella haters.” Andrew Barber, founder of Fake Shore Drive, the blog of record for Chicago’s surging hip-hop scene, breaks it down like this: “I think it stems from artists becoming big and people feeling like there’s only room for, like, one person to get through every few years.”

“Chicago hates you” is emblazoned on a T-shirt that debuted in 2009, the first official piece of apparel for Fake Shore Drive. Barber teamed up with three local streetwear brands—Leaders 1354, Enstrumental, and Eschmitte—to produce something that, like some hip-hop, bursts with bravado and teems with overstatement. “That shirt is—you can check the stats—the number one selling Chicago streetwear shirt of all time,” Barber says. “Period.”

Local rappers, taking note of the viral success of tees like “Chicago hates you,” are increasingly teaming up with designers in the city’s independent streetwear scene to gain exposure and build buzz. The relationship sometimes turns out to be the very boost a rapper needs—a sartorial, less seedy version of the renown imparted on a hip-hop artist when his track starts getting regular strip club play in places like Atlanta.

Hip-hop and streetwear have been intertwined at least since RUN-DMC first rapped about their Adidas. For national brands, working closely with up-and-coming musicians is part of a strategy that pairs advertising with artists in a joint effort to reach a bigger audience. Scion, Toyota’s youth-oriented vehicle line, has funded and distributed electronic, metal, and rap albums. Converse is now constructing musical collaborations, most recently the Gorillaz, Andre 3000, and James Murphy track “Do Ya Thing.” Mountain Dew’s Green Label Sound released the Cool Kids’ long-delayed official debut, 2011’s When Fish Ride Bicycles. Reebok recently dropped the critically acclaimed Action Bronson and Party Supplies mix tape, Blue Chips.

Mikhail Bortnik, co-owner and creative director for NYC brand Mishka, is leading the charge among the nation’s independent streetwear brands that have partnered with hip-hop stars, releasing mix tapes by celebrated acts such as Das Racist, Main Attrakionz, and Mr. Muthafuckin’ Exquire. As with most independent companies, the focus has always been making sure their clothing gets to the right artists in the hopes that they’ll wear it—preferably onstage or in a video. Chicago brands have seen their designs worn by the likes of Kanye West, Little Brother, Raekwon, and Snoop Dogg.
“Return” by G.o.D. Jewels, Silken Leigh, ShowYouSuck, and Auggie the 9th – City of Win; on Thursday, May 10, when City of Win debuts its inaugural fashion line at Beauty Bar, the company will also hand out copies of W1N Vol. 1, a mix tape featuring a who’s who of rising local rappers.

City of Win is a passion project, an extracurricular brand run by folks who spend their regular nine-to-fives working at places as varied as Cassette Company Records and Energy BBDO ad agency. About a year ago cofounder Aaron Albarran, a graphic designer for, came up with his first design for what would eventually become City of Win’s clothing line: the Windy City Champion Tee, which features a gigantic, light-blue “C” hugging a red star. Albarran and Miguel Mora, a rapper and associate media planner for digital marketing company Digitas, started sharing the designs with Stefan Clark (founder of Cassette Company Records) and Greg Morrison (an account management and marketing executive for Energy BBDO), who wanted in on the evolving project. Even after all four founders were in the fold, they still weren’t exactly sure what City of Win would become.

“I thought of the name close to two years ago and didn’t know what it was gonna be,” Mora says. “I was thinking a cool song or musical project name or blog or something like that.”

“We’ve all just thrown ideas on the table and been like, ‘Oh, like, let’s make a mix tape, let’s make an album, let’s make some sweatshirts,'” Clark says. “And then it just kind of came together.”

The Chicago rappers who contributed tracks to W1N Vol. 1 include YP, who signed to Universal Republic in February; political-juke group BBU, who just released their critically acclaimed sophomore mix tape, bell hooks, through Mishka and Diplo’s label, Mad Decent; Really Doe, who won a Grammy earlier this year for his songwriting contribution to Kanye West’s “All of the Lights”; and one-man pizza party and blogbuzzing artist ShowYouSuck.

“We were really trying to make—I don’t want to say the definitive, I want to say a definitive—Chicago tape,” Clark says. “To say that everybody on this tape is what’s going on in Chicago, that would be a rude thing to say because that’s bullshit. But we have a definitive Chicago tape.”

It’s the right time for any kind of Chicago-centric mix tape. “Right now is probably the best I’ve ever seen it in Chicago as far as on an indie scene,” Barber says. “There are so many artists that are hot, that are signed—or secretly signed—to major labels right now. It is very reminiscent of ’04-’05 when Kanye first blew up.”

The Chicago hip-hop scene blew up in a big way on March 12, when Chief Keef, a 16-year-old south-side rapper who experiments with the bombastic southern style known as trap, released his second mix tape, Back from the Dead. (Gawker published a profile on the young rapper, “Hip-Hop’s Next Big Thing is On House Arrest at His Grandma’s,” the same day.) Keef had gotten cosigns from the likes of Lil B and Soulja Boy, and had racked up more than a million views for his “Bang” video on YouTube, but the Gawker piece hastened Keef’s ascendency, and, to a certain degree, that of many up-and-coming Chicago rappers.

Describing the aftermath of a promotional video for Keef posted in January on WorldStarHipHop—”a website that hosts hip-hop-related videos for an estimated two million unique viewers per day”—the story goes on to state that “what’s unique about Keef’s rise is just how late in the game the wider Internet world has caught on. The WorldStar video was just the right match to light a fuse that had already been primed. Now that it’s lit, it’s revealed an entire subculture that’s been invisible for years.”

“There’s no longer a Tower Records or Virgin store where you can have parties or signings when mix tapes drop. The streetwear stores gave people a place to hang out.”—Andrew Barber,
Fake Shore Drive

Now major labels are hovering around the scene, with A&R reps keeping a close eye on the artists who show up in Fake Shore Drive’s most popular posts. “They’re watching everything that’s going on right now,” Barber says. Young Chop, who produced a number of Keef’s bangers, signed a production deal with Warner Brothers in early April. Lil Reese and Lil Durk signed with Def Jam a few weeks later. Keef hasn’t been signed just yet, but considering Kanye West just released a remix of Keef’s “I Don’t Like,” it seems all but certain he’ll land a sweet deal.

“It’s a really exciting time,” Barber says. “And it’s an exciting time for the streetwear brands too, because they piggyback off of each other.”

The heart of the Chicago streetwear scene lies in independent boutiques such as Leaders 1354, Saint Alfred, and Jugrnaut, which sell wares from national and local brands. These stores have also been home to the city’s underground hip-hop community, helping promote new and established artists with in-store events, advertising for concerts, and playing the latest mix tapes and albums.

“There’s no longer a Tower Records or Virgin store where you can go have parties or signings when mix tapes or albums drop,” Barber says. “When those went away, the streetwear stores or the boutiques kind of gave these people a place to go hang out. It’s almost like a barbershop; people talk about music, they talk about fashion, they talk about everything.”
“Remember Me” by ShowYouSuck, G.o.D. Jewels, Chandler London, Mig Mora, Auggie the 9th, and BBU’s Mr. Goodbar, Epic, and Illekt –