By Hannah Resnick
Medill Reports

Shoppers in Wicker Park got a peek into Vintage House Chicago’s flagship location at their opening party on March 21, following a soft opening on March 15.

Among the available clothing, a cartoon mural of a woman talking on a rotary phone with a cut cord among a tiger, ladybugs and other creatures stretched across one wall, and a triangular light resembling a rack of pool balls glowed from another. An analog photo booth from Auto Photo captured people’s memories from the party.

Generation Z and millennial shoppers may be familiar with Vintage House Chicago as a lively pop-up, but Maddie Rogers, 28, officially cut the ribbon for her first store in March, turning Vintage House from a bimonthly marketplace into a weekly one at 1433 N. Milwaukee Ave. On weekends, the shop will feature dozens of vendors, and during the week, Rogers will sell Primaries Vintage, her curated clothing line. Rogers’ grit and passion for vintage clothing helped her create an expanding business.

“Giving people clothes that make them feel good is what matters to me more than selling a bunch of stuff,” she said.

Rogers runs about 20 marketplace events each year, manages Primaries Vintage, rummages through up to 220 vendor applications per event and posts daily updates to more than 50,000 Instagram followers about the events and what she calls her “very funny and weird job.”

In a promotional poster for the opening, a cartoon version of Rogers said, “I’ve spent years searchin’ for vintage pieces, so you don’t have to!”

Rogers’ eclectic taste will differentiate Vintage House from its competitors on “oversaturated” Milwaukee Avenue, said Alexandria Jones, owner of Fad2Fresh, an Andersonville vintage store that frequently vends at Vintage House.

“One day she can be ‘70s, and one day she can be a ‘90s biker person, and she plays pool and does rock climbing,” Jones said.

Rogers also knows how to be a restaurant server and host, a bartender and an ice cream scooper – a few of her other past jobs that taught her to be good with money and customer service. In 2019 and 2020, Rogers and her roommates ran a concert venue outside of their Logan Square apartment, with events reaching up to 150 people.

Rogers began hosting vintage marketplaces in her Logan Square backyard in 2021, just two years after graduating from the School of the Art Institute of Chicago. She organized her first official market at the Logan Square Auditorium that December.

“And then it kind of just kept going, and I just kept booking,” she said.

She additionally worked briefly for a private art handler and the Museum of Contemporary Art before pursuing Vintage House and Primaries Vintage full time in 2023.

Sometimes Rogers said she earned little to no money because the turnout was small.

“Events are either very isolating or very rewarding,” Rogers said. “That level of inconsistency is really jarring, even when the highs are really high.”

Still, many vendors find the markets profitable. Chris Esteban, owner of Chris Thrifts, said he was making a few hundred dollars per event selling at flea markets, small pop-ups and “random art things” before he discovered Vintage House.

At his first Vintage House event, he brought in “over a grand in a day.”

“Maddie was really the catalyst (for) me feeling like I could actually do this full time,” Esteban said. “It felt as if I leveled up in real time.”

Rogers said she focused on the quality of attendees rather than quantity.

“I’d rather build a clientele of people that are like: ‘I’m here to spend money, I’m here to support these vendors, I’m here to be kind to everyone,’ and I think that I’ve been able to do that,” she said.

Despite the inconsistency of her income from the markets, Rogers earns enough as an event planner to sell only things she likes.

“If I’m doing this, I want to be excited about the things I’m selling, and I want to be excited about who’s buying it. I want to be able to genuinely be like, ‘Oh my God, I’m so happy you’re getting this thing.’”

Primaries Vintage sells an eclectic mix of vintage products including formal wear and home goods.

“I do masc and femme wear,” Rogers said. “It is really a little bit of everything.”

As the sole person in charge of planning Vintage House, Rogers said she feels pressure to ensure vendors make a profit but understands it’s out of her control.

“When I arrive, she’s usually scrambling like a chicken with his head cut off,” Esteban said. “Seeing Maddie with a coffee in her hand and two empty cups behind her, I’m like, ‘Oh yeah, she’s on top of her s*** right now.’”

To reduce pressure ahead of the store’s opening, Rogers recently hired her first employee. Anna Claire White, an illustrator and a bass musician in rock band Pinksqueeze, will work at the store and help with online marketing.

“I need people who can represent me and what I’m doing very well, and I trust Anna to do that,” Rogers said. “I’m going to not hire (more) people until I’m like, ‘Yeah, I trust you. You can talk to the vendors and be respectful.’”

Rogers also raved about award-winning cartoonist Caroline Cash, a good friend of hers, who designed the brightly colored posters for Vintage House.

“If she hadn’t agreed to do it, I just don’t think it would have been the same,” Rogers said. “She could be doing a million other things, but she’s doing my posters, and she’s my friend, and that’s really cool.”

Cash’s most recent poster promoted the store’s opening with a heart-eyed fan gawking at a cartoon version of Rogers and saying, “One girlboss against the world … I’m rooting for her …”

Hannah Resnick is a graduate student at Medill.