The Origins of The Illinois Vintage Fest

A brisk but sunny Saturday in March. After parking in the grass lot, you hop out of your car and join the constant stream of people moving up the hill toward the event center. The door swings open, and the music and hums of a hundred different voices pour out. Welcome to the Illinois Vintage Fest 19’.

On March 23 and 24, I attended the Illinois Vintage Fest for the first time alongside hundreds of other attendees. The building was filled with a warm and inviting atmosphere, feel-good songs, and each person had a child-like wonder on their face as they made their way from booth to booth.  

Couples held hands, friends goaded friends into buying that coat that they really wanted, and children got their first taste of the magical world of vintage clothing. 

Despite all attempts to resist and simply be an observer, I went home with a vintage skirt for only $20, which in my experience was a deal.  

After leaving the venue Sunday afternoon, I wanted to peek behind the curtain and hear more about how this all came to be. Cut to a few weeks and one fascinating interview later, and I have the real story behind the Illinois Vintage Fest, thanks to one of its founders, Shayne Kelly. 

On Easter Sunday, Shayne Kelly joined me via Zoom for an interview where he gave me the history of the Illinois Vintage Fest. Kelly shared the story of how he went from selling vintage clothes out of his parent’s garage to hosting over 100+ vendors in the DuPage Event Center. 

Kelly graduated from Lewis University in 2017 with a bachelor’s degree in graphic design. During school, Kelly said he transformed his degree into “being kind of this Swiss army knife of marketing.” 

Post-graduation, Kelly worked at RE/MAX Ultimate Professionals where he handled marketing for a couple of years until he went to work for CD One Price Cleaners in November 2019. 

Cut to April 2020, when he lost his job.

“I didn’t really leave,” Kelly said. “It was more or less due to COVID. I had no choice at the time.” 

After losing his job, he said he “applied to over 600 jobs, had over 100 interviews and nothing.” 

With little else to do, he took the extra money from his severance pay and went daily to different thrift stores and other secondhand places with his friends to find and buy cool old clothes.  

Then came the Black Lives Matter movement during the summer of 2020. 

“Me being a Black man, I wanted to help, but I couldn’t leave my house because my family members are immunocompromised,” Kelly said. 

Looking for another way to contribute to the cause, Kelly decided he could sell some of the clothes he had been buying and donate the proceeds. He set up a garage sale and was shocked by the 700 people who showed up at his parents’ house.  

A portion of the proceeds went to an organization called The Prison + Neighborhood Arts/Education Project, which works with prisoners in Statesville to get them access to classes about a variety of subjects, including the arts.  

Kelly felt that the PNAP was the perfect group for him to support since they were working to improve the lives of incarcerated people.

“Obviously, with the prison complex system, a lot of the inmates are people of color,” Kelly explained. 

After the success of his first garage sale, things started to take off. They had their first event, which they originally called Joliet Vintage Fest, right in Kelly’s front yard, where 10 of his friends all set up and sold clothing in a group garage sale. 

“Then out of that spurred Illinois Vintage Fest, which then spurred Prison City, which then spurred heyday,” said Kelly.  

When asked about the naming of Prison City Vintage, Kelly said that it was “derived from a few things, the Blues Brothers, which is what Joliet is known for, and its prisons, which is what Joliet is also known for. It’s not a bright spot in Joliet’s history, but it cannot be erased.”  

Kelly explained that the name also has a connection to his dad who was “a victim of the war on drugs, he also was in Statesville for a short period of time.”  

Bearing the name is not always easy, as Kelly said they “have caught some flak from people, so it’s not all sunshine and rainbows.” 

Some people even go as far as to imply the name is in poor taste or virtue signaling.  

Kelly values helping others over his own personal profit or gain, and he sees the potential in Joliet and wants to help it grow by building more businesses like his own Prison City Vintage. 

“That amazing city that I know is down there somewhere deep inside, but it just needs some help,” Kelly emphasized, noting that he is hopeful after the election of Joliet’s new mayor.  

After getting to know one of the founders — hearing his story, learning of his heart for his cause, and feeling the community that is so naturally fostered at his events — I plan to continue attending more events in the future.