Real talk? I’m not terribly prone to FOMO—I’m grown, respectably connected and have done my share of thangs, so to speak. Nevertheless, I must admit to feeling some significant event envy last fall when my press invite to ComplexCon once again got lost in the mail (and I may or may not have sent a few admonishing emails around, as a result), because it was not an event to miss.

Now in its fourth year, the two-day festival has been dubbed “the cultural Super Bowl” by the event’s producers and the team at the Marc Ecko-founded media platform—and with Lena Waithe, Issa Rae, Pharrell, and Virgil Abloh among the big names on the bill last November in Long Beach, Calif., I’m inclined to agree.

Thankfully, this year, I won’t have to miss out; for the first time, ComplexCon is coming to my hometown of Chicago this weekend, July 20-21, having kicked off its visit on July 15 with its first-ever weeklong initiative of community service, aptly called Complex Community. Thrilled that the streetwear culture spectacular will be within spitting distance of my apartment—and that the week’s events are being produced by two women of color—on behalf of The Glow Up, I wanted to catch up with ComplexCon’s executive producer, Isis Arias Clermont, and the director of Complex Community, Nicole Russell, to find out why the “Second City” became the second destination for this groundbreaking event.

Hip Hop duo Rae Sremmurd perform at the 2018 ComplexCon-Day 1 at Long Beach Convention Center on Nov. 3, 2018, in Long Beach, Calif.
Photo: Earl Gibson III (Getty Images)

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The Glow Up: For the uninitiated, what is ComplexCon, and how did it start?

Isis Arias Clermont, executive producer of ComplexCon: ComplexCon is an experience unlike any other. We call it our “Cultural Super Bowl”—making URL IRL—but in truth, it is a way for us to bring our audience an opportunity to connect, shop, see new art and discover new artists, vibe out to musical performances and DJs, check out panel discussions and eat amazing food by vendors curated by our First We Feast team. We are very intentional in delivering an array of experiences that speak to the cultures we’re passionate about, including hip-hop, streetwear, art, food, and culture in general.

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TGU: Why was Chicago chosen as the newest venue? How do you think this community will specifically benefit?

IAC: Chicago is a culturally rich and diverse city and one of the places that helped birth the cultures Complex covers. (Editor’s note: You already know!) So much creative energy comes out of Chicago and we have worked with many creatives and artists that have originated from here. Our collective interests in sneaker culture, hip-hop, and various forms of art meant that Chicago was not a city we wanted to fly over while traveling between the coasts, but one we wanted to celebrate.

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Isis Arias Clermont, executive producer of ComplexCon
Photo: Complex

Chicago is also the kick-off of our very first Community Week efforts. Highlighting and working with some of the local organizations that are doing great work in the city was an initiative we felt really strongly about. While our main event is two days and jam-packed with programming and exciting moments, we felt we could and should do more to create a lasting impact on the community by partnering with local organizations ahead of the convention.

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Nicole Russell, director of Complex Community: While planning our first Community Week it was important that we reached out and asked the people of Chicago what they need. Helping is made simple when you ask someone exactly what they lack and what will make them feel seen. As we planned Community Week, we made it a priority to produce collaborative events with Chicago-based brands and companies so we could bring people together. We’re challenging everyone to continue the work beyond ComplexCon. The benefits will be seen not only during the week but there will be long-term impact as well.

TGU: What can attendees expect this weekend? What will they not expect?

IAC: Attendees of ComplexCon Chicago should expect to have FUN. It’s a new environment built just for this moment. This is not a typical event. We are more than a music festival, we are more than a shopping experience; ComplexCon is an opportunity to commune with creators, participants, and fans of culture.

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Some specific things to expect include exclusive product drops and collabs that you would only see at ComplexCon, celebrity appearances and fun surprises. We also have Complex Current, a series of fireside chats, which is a new set of programming for Chicago, in addition to Complex News Presents, real-life discussions of topics that we can dive deep into.

A few of our hit shows will also be on-site live, which gives fans to get a chance to engage in real-time with the content they love and meet some of our on-air talent.

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TGU: On a more personal note: As women of color producing an event of this magnitude, what are you hoping to contribute to the proverbial “culture” via ComplexCon Chicago?

NR: Isis and I worked closely to plan something special for everyone and those efforts will be seen and felt. I personally invited 250 guests from underserved communities to ComplexCon because we wanted to make sure everyone had access. There’s no telling how that experience will inspire and impact our future top-selling designers, artist or world-class chefs. I’m providing access with the hope that it will translate to opportunity.

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Nicole Russell, Director of Complex Community
Photo: Complex

IAC: We are both very invested in the youth and supporting women. I am interested in creating opportunities for those who have been doing the work already and dream to go beyond. Whether that’s who we have partnered with on Community Week, or our local food and experience vendors—our efforts should help support the journey they’re already on. I don’t take credit for the success of others but always hope that we can be a part of that story. If ONE connection is made while at ComplexCon that didn’t exist before—if a memory is made and a moment is cherished, a business grows, or one of our youths embarks on a new opportunity, I will be proud of the work we’ve done.

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TGU: What do you hope attendees will take away from the experience—and will Chicago be a regular venue in years to come (fingers crossed)? 

IAC: We want everyone to leave feeling full. Full because they copped some new exclusives, discovered a new brand, checked out a new artist or watched a favorite, sat in one of our talks and learned something new, had a shared experience, gained a new friend, explored a new restaurant and ate some delicious food.

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Chicago is a special city, and we’re happy that it was our first exploration outside of our flagship. We hope to continue to build on the opportunity to do more here in the future.

The Glow Up tip: ComplexCon Chicago will take place at McCormick Place on Saturday, July 20 and Sunday, July 21. You can get see the event lineup, vendors and buy tickets ($80-$300) on their website.