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."
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 – is a barbershop, as well as a retail space and gallery. Open since Halloween, the brand’s founders hope to provide a space to engage neighborhood kids, and Leaders provided the blueprint for the boutique. “We’ve been messing with them guys for a couple years now, going shopping there for a while,” says B.R.E.A.D. cofounder Gustavo Diaz. “They inspired me to do what we’re doing today and I would love to have a place like that out this way, where I’m from.”

Right now B.R.E.A.D. sells clothing from its own line and Local Motives, a brand launched by Chicago newcomer Brian Longwill. The 23-year-old draws inspiration from his new home—Longwill’s “Air Freddie” crew neck recasts Queen’s theatrical front man onto the iconic “Air Jordan” symbol—but he grew up with the streetwear and hip-hop scenes in his hometown of Pittsburgh. “The main shop back home is called Time Bomb,” Longwill says. “Mac Miller, Wiz Khalifa, those artists came out of that store.” (The pair are coheadlining a summer tour that stops by First Midwest Bank Amphitheatre on Fri 7/27.)

Miller’s recent Blue Slide Park, became the first independent album since 1995 to debut at number one on the Billboard 200. “I remember seeing a Mac Miller flyer of him when he was 16,” Longwill says. “I laughed and said, ‘What is this?’ But he was persistent and steady and kept going to Time Bomb and kept working with the music. He really came up through there, as well as Wiz.” Khalifa’s monster hit “Black and Yellow” topped the Billboard singles chart in 2010. The song’s video, which has generated more than 126 million views on YouTube, features a bystander wearing a shirt by a Pittsburgh brand called Blasfome, which is also sold out of Time Bomb; Longwill says the video was so successful for Blasfome, the designer bought a brand-new BMW off of it.

When Longwill moved to Chicago last August, he knew just what he needed to do to learn the lay of the land. “I came out here and went to Jugrnaut,” he says. “The first or second day in Chicago, I walked in and said, ‘Who are the artists I need to find out about?'”

“You could walk into a shop and hear what’s playing and know that’s what’s in right now—or that’s about to be in right now—because a lot of the people who run the shops are tastemakers,” says Clinton Sandifer (aka ShowYouSuck). “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.”

Beyond that, local stores also help artists through publishing blog posts and videos, and offering a physical space for aspiring MCs and producers to leave free mix tapes for curious shoppers. “It’s definitely not responsible for all of the ill shit that’s coming out of Chicago, but it’s one form of promotion,” says Chancelor Bennett, aka Chance the Rapper. “The streetwear stores in Chicago definitely have supported and help push the Chicago artists on the rise right now.”

Chance is one of the more sought-after rappers on the scene since he dropped his #10Day mix tape in April, and he credits stores like Leaders for helping him get his start. “The end of ’09 I had a mix tape that nobody knew about,” Bennett says. “Leaders threw me a listening party. It was a small gathering of people.”

Leaders threw Chance another listening party in the fall, and Bennett says 300 people showed up—and that an additional 100 weren’t able to get in.

“We mess with the artists that mess with us, unconditionally, whether you have a huge fan base or you’re dropping off a stack of mix tapes and still trying to get heard,” says Leaders’ creative director Vic Lloyd. “I’m not here just to benefit, I’m here to support. I remember a lot of these guys when they was just shorties, and they didn’t even know they wanted to rap or nothing.”

When #10Day dropped April 3, Jugrnaut hosted the official listening party, and 400 people came through. Now other brands like B.R.E.A.D. are looking to give Bennett new tees so that he can expand their scope. It’s a full-circle methodology for fashion lines to gain more exposure.

“We’ve been hooking a lot of people up for years,” says Joseph “Fresh Goods” Robinson, cofounder of streetwear lines Vita Morte and Dope Boy Magic. “You about to be in a video? Here’s a T-shirt.” Robinson and Vita Morte cofounder Terrell Jones hatched the concept back in 2001 when they attended Lane Tech College Prep High School. “It wasn’t a lot of people doing the things we was doing,” Robinson says. “This is Lane, everybody trying to be a rapper or think they’re gonna be in the NBA. We’re, like, the first people that say, ‘Hey, we’re gonna do a T-shirt brand.'”

“We mess with the artists that mess with us, regardless of whether you have a huge fan base or you’re dropping off a stack of mix tapes and still trying to get heard.”——Vic Lloyd,
Leaders’ creative director

Jones, who does freelance graphic design for other streetwear lines, and Robinson, who’s also a brand ambassador for Adidas, have hosted one-off events and parties to help promote the Vita Morte brand, and their latest venture is a Monday-night event at 6 Corners bar called Feed the Homies. Between Vita Morte and Robinson’s project with Vic Lloyd, Dope Boy Magic, the young entrepreneur has amassed a solid lineup of local artists wearing his stuff: YP, Rockie Fresh, Vic Mensa and Greg Landfair of Kids These Days, Chance, Caleb James, and Alex Wiley. And that’s before taking into account the high point his Dope Boy Magic “Trill” shirt reached at Coachella this year.

“BJ the Chicago Kid rocked Coachella with Snoop,” Robinson says. “So I just gave him [a shirt], overnighted it, and he and Snoop wore it.”

On Monday, Dope Boy Magic debuted a new line with Fake Shore Drive, a series of shirts made for young local artists with cult followings. The subject of the first T-shirt is GBE’s Fredo Santana, and its tagline—”Fredo in the cut, that’s a scary sight”—comes from a verse off Chief Keef’s “I Don’t Like.”

Dwamina K. Drew, a close associate of Robinson and Jones, is a designer who launched Enstrumental in 2006. (Until recently, the three shared a space in Pilsen’s Lacuna Lofts.) Drew likes to produce sharp, simple designs that draw from hip-hop and social consciousness; he made what he calls the first Obama-inspired streetwear tee and donated 8 percent of the proceeds to the 2008 campaign. The design was one of three under consideration to become the official T-shirt for that presidential run.

Drew’s also created a tee called “rap minus lies equals hip-hop,” a design so popular he’s had to send out some 13 cease-and-desist letters to stop others from printing it; beloved North Carolina hip-hop act Little Brother took that shirt on tour with them shortly before breaking up. And Drew collaborated with Lupe Fiasco and streetwear brand FTK on a shirt celebrating the release of his 2006 Grammy-nominated debut, Food & Liquor.

Jugrnaut has developed its line partially with the help of a variety of rappers, partnering with Raekwon on a hat and with Pac Div and Chip Tha Ripper on some tees. Recently Jugrnaut worked with Million Dollar Mano on an embroidered Starter snapback hat for his latest project, a loose collective called Treated Crew. Mano served as the tour DJ for Kanye West and Jay-Z’s epic Watch the Throne trek, and he hooked West up with one of the Treated caps. Photos of West wearing the Treated cap began circulating online as far back as January, no doubt fueling the demand for it before it went on sale. Jugrnaut made 68 hats, and put 30 of them online at midnight on Tuesday, February 28; co-owner Manny Rodriguez says that the first round sold out in about a minute, and the whole stock disappeared soon after.

Jugrnaut’s next local collab is with ShowYouSuck; they plan to release a tee and cap, and they’ve recently hit upon the design. “I was like, ‘Yo, I got an idea,'” says Jugrnaut designer Brian Nevado. “‘How about we put you on the couch with Beavis and Butthead sitting in the middle, and you’re drawn out like Beavis and Butthead?’ He really dug that.”

The relationship ShowYouSuck has established with Jugrnaut not only helps advance both parties’ individual product, it also further develops their respective brands. According to Clyde Smith, a feature writer for music industry and technology site, the return on investment is more intangible than, say, what a traditional record label is looking for. But that investment still has value. “Having relationships with bands and even putting out music isn’t about making money off the music so much as getting some of the cool associated with the band,” Smith says. “So it’s really a branding strategy.”

“Branding” has long been a dirty word in certain independent music scenes, many of which have fostered an anticorporate ethos. Smith says those attitudes are starting to shift, and that artists increasingly view branding as imperative for anyone seeking to make a living through music. “Indie artists, even people signed to indie labels, are having to really explore alternative revenue streams—not to supplement their music sales, but really to replace the drop in music sales,” Smith says. And a variety of companies—including streetwear brands—are helping provide musicians with options. “The relationships with brands are becoming really important, not only for revenue but also for marketing themselves.”

This kind of synergistic relationship has been an important part in the development of hip-hop—perhaps more so than is the case with other genres. Plenty of rappers have long welcomed financial success—and the choice streetwear brands that help them achieve it—with open arms. According to Smith, it’s a blueprint that other musical genres, and companies that share their sensibilities, need to study.

Smith says brands are getting smarter about partnering with the right artists, but there have been some slipups along the way. Scion caught some flak when it released an EP by Washington, D.C., trio Magrudergrind in late 2010; the band plays a style of metal called grindcore, a brutal subgenre that’s long been tethered to anticorporate sentiments, and many fans and musicians balked at the very idea of such a partnership.

With W1N Vol. 1, City of Win’s founders aim to develop the kind of partnerships needed to get a leg up in an oversaturated music and fashion marketplace. The company has been promoting the compilation by dropping individual tracks every Wednesday since April 4, with the exception of YP’s joint with Calliko, “Let Me Smoke,” which was released just after YP signed to Universal. (“The song came out and his label said, ‘No more songs can come out,'” Morrison says.)

“Let Me Smoke” got picked up by hip-hop and R&B station WGCI, and other W1N Vol. 1 tracks have gotten some exposure. ShowYouSuck says his song “Trilluminati” (which features Mora and female rapper Henny B.) fell into the hands of New York radio station Hot 97. G.o.D. Jewels’s “Gym Shoes” landed on shoe-centric and fashion-focused sites including Modern Notoriety.

As City of Win’s founders hustle to expose Chicago hip-hop and streetwear culture to the rest of the world, they’ve found that while competition in the crowded national arena is fierce, there’s still room to grow in Chicago and beyond—no hate necessary.

Correction: This story has been amended to reflect that is was a bystander in the “Black and Yellow” video, not Wiz Khalifa himself, who wore a Blasfome shirt, and that the Blasfome brand, though sold at the Pittsburgh shop Time Bomb, was not created by the shop’s founders.