{"id":105162,"date":"2025-04-02T09:54:50","date_gmt":"2025-04-02T14:54:50","guid":{"rendered":"https:\/\/news.medill.northwestern.edu\/chicago\/?p=105162&preview=true&preview_id=105162"},"modified":"2026-01-01T16:05:49","modified_gmt":"2026-01-01T22:05:49","slug":"old-clothes-new-store-vintage-clothing-entrepreneur-opens-permanent-location-in-wicker-park","status":"publish","type":"post","link":"https:\/\/news.medill.northwestern.edu\/chicago\/old-clothes-new-store-vintage-clothing-entrepreneur-opens-permanent-location-in-wicker-park\/","title":{"rendered":"Old clothes, new store: Vintage clothing entrepreneur opens permanent location in Wicker Park"},"content":{"rendered":"\r\n

By Hannah Resnick<\/strong>
Medill Reports<\/em><\/p>\r\n

Shoppers in Wicker Park got a peek into Vintage House Chicago\u2019s flagship location at their opening party on March 21, following a soft opening on March 15.<\/p>\r\n

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\u2019s memories from the party.<\/p>\r\n

\"\"
The photo booth inside Vintage House Chicago. (Hannah Resnick\/MEDILL)<\/figcaption><\/figure>\r\n

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\u2019 grit and passion for vintage clothing helped her create an expanding business.

\u201cGiving people clothes that make them feel good is what matters to me more than selling a bunch of stuff,\u201d 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 \u201cvery funny and weird job.\u201d

In a promotional poster for the opening, a cartoon version of Rogers said, \u201cI\u2019ve spent years searchin\u2019 for vintage pieces, so you don\u2019t have to!\u201d<\/p>\r\n

\"\"
Poster promoting the opening of Vintage House designed by Caroline Cash; via @vintagehousechicago on Instagram<\/figcaption><\/figure>\r\n


Rogers\u2019 eclectic taste will differentiate Vintage House from its competitors on \u201coversaturated\u201d Milwaukee Avenue, said Alexandria Jones, owner of Fad2Fresh, an Andersonville vintage store that frequently vends at Vintage House.

\u201cOne day she can be \u201870s, and one day she can be a \u201890s biker person, and she plays pool and does rock climbing,\u201d Jones said.

Rogers also knows how to be a restaurant server and host, a bartender and an ice cream scooper \u2013 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.

\u201cAnd then it kind of just kept going, and I just kept booking,\u201d 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.

\u201cEvents are either very isolating or very rewarding,\u201d Rogers said. \u201cThat level of inconsistency is really jarring, even when the highs are really high.\u201d

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 \u201crandom art things\u201d before he discovered Vintage House.

At his first Vintage House event, he brought in \u201cover a grand in a day.\u201d

\u201cMaddie was really the catalyst (for) me feeling like I could actually do this full time,\u201d Esteban said. \u201cIt felt as if I leveled up in real time.\u201d

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

\u201cI’d rather build a clientele of people that are like: \u2018I’m here to spend money, I’m here to support these vendors, I’m here to be kind to everyone,\u2019 and I think that I’ve been able to do that,\u201d she said.

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

\u201cIf I\u2019m doing this, I want to be excited about the things I\u2019m selling, and I want to be excited about who\u2019s buying it. I want to be able to genuinely be like, \u2018Oh my God, I’m so happy you’re getting this thing.\u2019\u201d

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

\u201cI do masc and femme wear,\u201d Rogers said. \u201cIt is really a little bit of everything.\u201d
\"\"
As the sole person in charge of planning Vintage House, Rogers said she feels pressure to ensure vendors make a profit but understands it\u2019s out of her control.

\u201cWhen I arrive, she’s usually scrambling like a chicken with his head cut off,\u201d Esteban said. \u201cSeeing Maddie with a coffee in her hand and two empty cups behind her, I’m like, \u2018Oh yeah, she’s on top of her s*** right now.\u2019\u201d

To reduce pressure ahead of the store\u2019s 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.

\u201cI need people who can represent me and what I’m doing very well, and I trust Anna to do that,\u201d Rogers said. \u201cI’m going to not hire (more) people until I’m like, \u2018Yeah, I trust you. You can talk to the vendors and be respectful.\u2019\u201d<\/p>\r\n

\"\"
Merchandise for sale at Vintage House Chicago. (Hannah Resnick\/MEDILL)<\/figcaption><\/figure>\r\n



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

\u201cIf she hadn’t agreed to do it, I just don’t think it would have been the same,\u201d Rogers said. \u201cShe could be doing a million other things, but she’s doing my posters, and she’s my friend, and that’s really cool.\u201d

Cash\u2019s most recent poster promoted the store\u2019s opening with a heart-eyed fan gawking at a cartoon version of Rogers and saying, \u201cOne girlboss against the world \u2026 I\u2019m rooting for her \u2026\u201d

Hannah Resnick is a graduate student at Medill.<\/em><\/p>\r\n","protected":false},"excerpt":{"rendered":"

By Hannah ResnickMedill Reports Shoppers in Wicker Park got a peek into Vintage House Chicago\u2019s flagship location at their opening party on March 21, following a soft opening on March 15. 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