The Pop-Up: A homegrown space for Chicago’s creatives

Kevin and Molly Woods run The Pop-Up, a resale boutique and creative outlet for local artists, nestled in Chicago's Wicker Park neighborhood. Credit: Jesus J. Montero

Jesus J. Montero is an award-winning journalist and passionate storyteller. He's known for his investigative work covering social justice, music and culture. Jesus J. is also a producer, curating dynamic experiences that highlight culture through storytelling and dialogue. You can follow him on Instagram at @JesusJMontero. Photo: Olivia Gatti

Freedom and legacy go hand in hand. For entrepreneurs, it means building something that reflects not only their vision but also the stories they want to share with the world.

Husband-and-wife Kevin and Molly Woods embody that philosophy. Their partnership began with a LinkedIn message - one that didn't lead to a job, but to something much bigger. She was a recruiter," Kevin recalled. You know those messages you always think are a scam? Well, that's how we met. She sent me one of those 15 years ago, and we've been together ever since."

A new era of creatorsThe Pop-Up blends style with community-focused retail in Chicago's Wicker Park. Credit: Jesus J. Montero

Fast forward to today, Kevin and Molly now run The Pop-Up, a resale boutique and creative outlet for local artists, nestled in Chicago's Wicker Park neighborhood. The store's mission is rooted in the spirit of collaboration and community. But that path hasn't been without challenges.

This space is more than just a store. It's our home," Molly shared after their shop was broken into - twice. Yet, through it all, they stayed resilient. The space, once home to the iconic RSVP Gallery where creatives like Don C and the late Virgil Abloh once shaped Chicago's cultural scene, is now a hub for a new generation of artists and collaborators.

This isn't just about selling clothes," Kevin emphasized. It's about creating a space where ideas take flight, where people can come together to celebrate the boundless creativity in this city."

A vintage yellow Sade t-shirt hangs in The Pop-Up boutique. Credit: Jesus J. Montero

Both Kevin and Molly come from backgrounds in HR, and while they found success in the corporate world, it never quite felt like enough. We were both HR professionals for years," Kevin explained, but we wanted to create something of our own."

A trip to Japan in 2019 was pivotal. That trip changed everything for me," Kevin said. I came back inspired to create something of my own. I secured the domain as soon as I landed, and that's when The Pop-Up was born."

A community-driven comeback

Their dream became a reality, but not without hurdles. After the break-ins, The Pop-Up was forced to close its doors temporarily. However, the community they had poured so much into over the years rallied around them, providing support and encouragement. It was inspirational to see how everybody in the team rallied together, working through, being resilient, and patient. Knowing that there was light at the end of the tunnel," Kevin shared.

They're not just employees," Molly added. They're family. We've watched them grow, their talents blossoming right in front of us."

Kevin Woods, co-owner of The Pop-Up, organizes clothing on display in their Wicker Park boutique. Credit: Jesus J. Montero

The Pop-Up now thrives as a collaborative space, hosting local designers, artists and small businesses - each contributing to Chicago's vibrant creative scene. The internet has also played a role in cultivating this community. It's definitely a tool," Kevin said. It helps us connect. ... But at the end of the day, I still believe in that personal interaction to really connect and validate those relationships."

Now reopened with a fresh design and layout, The Pop-Up continues its mission of supporting local talent and fostering community. Kevin and Molly's journey is one of resilience and creativity, and their store stands as a testament to the power of collaboration.

Working with local people to do great things - that's how we started, and that's how all of this came to life," Kevin said, looking ahead to what's next for The Pop-Up.

With its doors open once again, The Pop-Up is ready to continue adding to Chicago's rich history and culture in fashion and beyond - one collaboration at a time.

An aerial view of Chicago's Wicker Park neighborhood, home to The Pop-Up boutique, with the downtown skyline in the distance. Credit: Jesus J. Montero

Chicago's small business owners are shaping their communities with purpose. In this series, we highlight the entrepreneurs behind local gems - each of them building something bigger than just a business. Through Solo, Mozilla's free AI-powered website creator, they're exploring new corners of their community online. Check out The Pop-Up founders Kevin and Molly Woods' Solo website here.

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