Can ComplexCon do justice to Chicago streetwear?

For its fourth year, the culture convention of style, arts, and music outlet Complex has branched out into a second home in Chicago. ComplexCon is coming thousands of miles from its home in Long Beach, California, bringing national attention with it—and the members of Chicago’s groundbreaking creative community have been feeling the weight of that attention differently. Some of them are reluctant to celebrate, not least because they’ve been doing for decades what ComplexCon is attempting for a weekend in July: as the convention’s website puts it, it aims to bring together “pop culture, music, art, food, sports, innovation, activism, and education.”

A swarm of vendors, artists, and designers will descend upon McCormick Place on Saturday and Sunday, July 20 and 21. Creatives from multiple mediums—especially streetwear, the event’s center of gravity—have been working on presentations and collabs, hoping to show off their work on an international stage that’s crowded with influencers, all of them trying to find pop culture’s next pivot. Among the countless exhibits, talks, and performances are exclusive merch releases, food pop-ups, and various displays and “experiences” from more than 100 brands. For every old, established company with no special connection to Chicago—Old Spice, Hennessy, Toyota—there’s a hometown heavy hitter such as rapper Taylor Bennett, visual artist Sentrock, and DJ King Marie. And they’re not the only ones getting ready to showcase what the Chicago art scene has to offer: the exciting young locals involved with ComplexCon include graphic designer and artist Brandon Breaux (the prime mover of the Invisible Space at 85th and Cottage Grove) and fashion designer Sheila Rashid.

Anticipation has been building for months, and though the commotion is warranted, ComplexCon has met with a mixed reception from locals. Chicagoans know they’re the ones who’ve put in the work that made the city a prime location for the event, and some of them worry that ComplexCon is just parachuting in to capitalize on their efforts. I’ve talked to several local artists who, while they don’t want to be quoted by name, feel the festival has fumbled its communications with the Chicago community. They say they don’t know what’s going on, and that ComplexCon has been reaching out to artists so late in the game that it can only piggyback on what they’re already doing—which would result in what’s basically a branding exercise, not a collaboration specific to the convention. If this is broadly true, that’s a shame, because ComplexCon and local organizers share a goal: they both want to find the best way to exhibit the city’s splendors while appealing to a broad audience.

One of those skeptical locals is Corey Gilkey, who founded and helps run Chicago clothing shop Leaders 1354. Opened in Hyde Park in 2002 and now operating out of a storefront in the West Loop, Leaders has been influencing fashion and culture all over the city for longer than most of its competitors have existed—all four founders of streetwear institution Fat Tiger Workshop, for instance, came through Leaders.

When I talked to Gilkey, it was a breezy Juneteenth morning, and he was feeling upbeat about that day’s season opener for Boxville, Chicago’s first shipping-container mall and street-food market. Cofounded by Gilkey and hosted by the Bronzeville Incubator under the 51st Green Line station, Boxville debuted in 2017, and during its inaugural summer it claims to have hosted 64 locally owned enterprises and more than 2,500 patrons. Since then the hyperlocal marketplace has grown to bring together even more Chicago entrepreneurs to serve visitors from Bronzeville and beyond.

But the news wasn’t all good. Many of Leaders’ previous collaborators, including ComplexCon darling Virgil Abloh, will be a part of the convention’s Chicago debut, but Leaders itself didn’t even get an invite.

“We weren’t approached—no e-mail, not a call,” Gilkey says. “You go to every other area, like New York and LA, and they’re gonna have some sort of independence around that. For people not to be offered that here is really a slap in the face, almost.”

He acknowledges that ComplexCon does important work, but he doesn’t know how it could overlook Leaders. “They’re the Super Bowl of streetwear and luxury and culture. They market themselves to be that,” he says. “I’m not gonna dis them for that—it’s something that needed to be done. They’re having an industry event about streetwear and sneakers and art and music. That’s dope—but all that shit starts with the independents.”

Fat Tiger Workshop cofounder Vic Lloyd, who created the brand’s Sensei arm, spent ten years at Leaders 1354, doing graphic design, running events, and pitching in with marketing. He’s DJing at the first Chicago ComplexCon, and his feelings about the event are significantly warmer. FTW, now in River West, launched on Black Friday 2013, and it follows in Leaders’ footsteps in its support for the community: the shop hosts local-focused events, develops spectacular collaborations with Chicago talent in all mediums, and keeps the same energy for its hometown despite its ascent to national renown.

“I started Sensei there a couple years ago at that store,” Lloyd says, referring to Fat Tiger’s previous location near Carpenter and Grand. “I was DJing before I got into fashion, but just as a hobby. It kinda became a necessity from throwing events. We was booking DJs and all that stuff, so one day I just decided to take it serious. I had a couple of homies that helped me out and gave me pointers along the way, and it turned into a thing I do too.”

Lloyd looks forward to the attention that will converge on the city the weekend of ComplexCon, which also includes the annual Chicago festival of international music-media outlet Pitchfork. For him, these worlds coming together is natural.

“Fashion, music, art . . . all of those things are a woven web. You can’t do one without the other. They all feed off each other,” he says. “It’s dope for something like ComplexCon to get into the city and showcase all those things and showcase it from a worldview, not just a local view. All those things go on every week here on a smaller level. You can always catch us doing something. Other shops doing stuff, like parties, pop-ups . . . it’s always stuff going on, but this is the first time it really got put on a huge stage.”

Gilkey might counter that Leaders 1354 has been logging the hours to make Chicago its own big stage for 17 years, and that for most of that time national outlets have neglected the city’s talent. He suspects that once the fest is over and gone, there won’t be any lasting benefits to locals. He doesn’t see ComplexCon hiring enough Chicago people or engaging with the scene here.

“We train youth and mentor them to be successful,” Gilkey says. “We want to give them the tools to be entrepreneurs one day. Businessmen, entrepreneurs, graphic designers, photographers, videographers—and none of this will be showcased at ComplexCon. Who’s gonna do the photography for them? Who’s gonna video and edit them? It’s gonna be someone from LA. That’s millennial culture and social-media culture right now—who has the hype? Who has the most? Instead of thinking, ‘Let’s give this guy an opportunity. Let’s shine on him for his work of ten, or 15, or even five years capturing Chicago. And introducing us to Chicago.’ We’re the heart of America. Everything goes through here.”

The influence of Leaders’ Hyde Park boutique will inevitably flow through ComplexCon, even though the shop won’t be participating. Gilkey has helped cultivate a lineage of stars in the fashion industry without getting national love for it, but the festival’s arrival in Chicago has become a catalyst for creatives—and he sees this as spurring a change that’s more in line with his goals. Folks left out of the big show, he says, are extra driven to collaborate with one another.

“Complex could have done some cool things,” he says. “But remember, they’re hoping the big companies come and showcase Chicago, when it’s the smaller guys without a Nike and Adidas account that are really runnin’ the streets or really hiring people. And the streets love them and what they represent. I wanna say thank you, ComplexCon, because what you did is inspire these kids to work together. I’m getting texts like, ‘Aye man, we gonna do this T-shirt. Let’s work together—we gon’ do this T-shirt, we gon’ showcase all the brands that’ve been supporting it. We look up to Leaders, we look up to Fashion Geek, and for you to not be here . . . it’s all on us now.'”

It remains to be seen if ComplexCon’s expansion to Chicago was a good decision, but there’s no doubt that the city’s influence on global fashion and culture is on the rise. ComplexCon may not be ready for Chicago, but Chicago is ready for anything.  v