Shopping for vintage clothing is like going on a stylish treasure hunt through time. Every rack holds a story, and every shirt or pair of jeans echoes with nostalgia. Whether you are channeling rebellious grunge vibes of the ’90s with plaid flannels or stepping back into the bold world of the ’80s with shoulder-padded blazers and gold chains, vintage fashion is all the rage. But vintage is not only about looking back. It is about sustainability, individuality, and making history wearable again.
In the city of Joliet, 30 miles southwest of Chicago, Prison City Vintage has become a destination for devoted vintage shoppers. Owned and founded by Shayne Kelly, the store offers a selection of retro styles spanning decades.
“We deal in all sorts of vintage clothing all the way to the early 2000’s,” said Shayne. “Our identity as a vintage store is everything. That’s what you get when you walk in the door. The vibe I’m trying to convey here is laid back, cool, and a place that you can go when you need a second to chill out and relax.”
In a world of mass-produced fashions, Prison City Vintage stands out by offering one-of-a-kind pieces.
“I think a lot of people love it because the way that the malls and new brands are set up there’s a lot of the same product over and over again, and it changes season by season, just a little bit.” explained Shayne. “A lot of people want to be unique and have unique identifiers. I think a lot of people want to be a little bit more individual versus being part of the collective.”
The store’s name carries deep meaning for Shayne. It is a nod to his father and a movie scene that is legendary in Joliet. The open of the 1980 hit movie, The Blues Brothers, takes place outside of the Old Joliet Prison, which was formally The Illinois State Penitentiary.
“The Blues Brothers was one of the most important things that showcased our little town of Joliet,” Shayne said with pride in his voice. “It was the greatest cameo in a movie of all time. So, we used that a lot in our imagery here at Prison City Vintage because we were taking the name from it.
“Prison City Vintage’s name came from my dad,” shared Shayne. “Me and my dad both came up with it together. My dad was a victim to the war on drugs in the ‘80s and ‘90s and spent some time in Statesville (prison), which he always dubbed Prison City, paying homage to the movie The Blues Brothers.”
Vintage is cool
Shayne started selling vintage clothing long before Prison City Vintage became a staple in downtown Joliet.
“I’d been selling vintage since 2013 online on eBay and a bunch of other places like Depop (vintage clothing website), and sometimes in person to my friends at Lewis University, where I went to school,” recalled Shayne. “A lot of people didn’t believe in it. They didn’t really appreciate its value as much as I did. But the generation after me really got into buying secondhand and adopting more sustainable practices, including buying secondhand clothing.”
Everything changed suddenly with a simple garage sale that took Shayne by surprise.
“We had our first garage sale in 2020 and had no expectations at all,” admitted Shayne. “I wanted to put all the clothing I’d collected over the past few months and years outside for people to look at. Everything that could go wrong, went wrong. Racks kept falling over. The wind wasn’t cooperating. I just put everything on the ground, blanketed it up, and watched it happen right in front of my eyes.”
To Shayne’s surprise, hundreds of people flooded the street to buy what he had put out for sale. As Shayne put it, “They were going nuts over dingy old T-shirts that I’d found in the dumpster.”
Plus, the timing of that sale was perfect and happened just as the Covid crisis was sweeping across the nation.
“That first garage sale started when Covid was setting in. Not a lot of people were going inside, shopping or even gathering at all,” remembered Shayne. “A lot of people were staying away from each other. We gave them an opportunity to shop very safely outside and allow them to look at something cool that they may have never seen before.”
The success of that sale marked a turning point. Freshly laid off from his graphic design job during the pandemic, Shayne faced a crossroads.
“I applied to over 500 different jobs all around the U.S., but then I decided to take this clothing thing more seriously,” recalled Shayne about what he was going to do next.
He became a relentless treasure hunter, scouring thrift stores, garage sales, and even dumpsters to build his collection. His next pop-up was held at his parent’s house in Joliet and drew thousands.
“After that, I saw it,” added Shayne. “I had to open a brick-and-mortar store.”
Prison City Vintage first opened in the nearby town of Crest Hill in 2021. For Shayne, launching a new business was an all new experience.
“When we first opened, there were a lot of complications including not knowing how to build things, getting the right permits,” Shayne recalled. “It wasn’t as easy as setting up a garage sale. We had to make it look presentable, and that was something new we had to learn as a team.
“Having never done anything like that before was scary, but I put all my eggs in one basket and opened Prison City Vintage.”
Then in 2023, Shayne decided to move Prison City to downtown Joliet where he grew up.
“We moved in just before the big construction projects started,” Shayne said. “A lot was changing, but we believed Joliet would come out stronger on the other side and create a community we could be part of.
“A lot of people looked at me very crazy because they knew the looming construction was coming with a new administration in town,” Shayne laughed. “But I had a great support system, my friends, my family, and of course, all the other vintage vendors in Illinois.”
For Shayne, vintage carries a deeper meaning than the merely selling clothes. Prison City is about his passion for nostalgia. While the store has vintage fashion from the 1970’s to the 2000’s, Shayne definitely has his favorite decade.
“I got into vintage because I grew up in the mid-to-late ‘90s, and the clothing is amazing. I love it,” said Shayne with excitement. “The ‘90s were very loud and abrasive, and the clothing encapsulated the culture amazingly. It was a time when everybody was unifying in the streets. Street style was at its peak, and new brands were popping up every day.”
Keeping vintage hip
Prison City Vintage is much more than just a vintage clothes shop. Shayne wants every visit to his store to be an experience for his customers.
“We sell more than vintage clothing,” Shayne explained. “We have spots where people can sit and hang out. Some come in every day to do homework. I’ve even helped kids from down the street with their school work. We’ve helped people get clothes when they’re down on their luck. I just want to help everyone out and keep my community safe.”
The vibe? Pure nostalgia. “Think of it like your brother’s bedroom in the ‘80s or ‘90s,” Shayne added with a grin. “You walk in and go, ‘Wow, this stuff is all so cool. I want stuff like this!’”
For Shayne, success also means putting himself out there, literally.
“One part of owning a business is being visible,” explained Shayne. “We work on content daily to survive in Joliet. I can’t go anywhere without being recognized from our Instagram videos. People love the store because I think they love me.”
The real magic is the connection to customers that Shayne makes every day.
“The most important thing is building relationships in the community,” shared Shayne. “The people who come in here are amazing. I hear different stories every day.”
The work to keep the store full of great vintage clothes is also a never-ending adventure. Shayne knows exactly where to look for the forgotten fashions others may not want.
“We have a lot of sources for our vintage clothing. We buy a lot from people that just walk in the store,” explains Shayne. “We do the thrift store thing where we go and comb thrift stores for hours. We also go to estate sales and garage sales. You name it, we’ve been there trying to get their vintage clothing.”
Once the inventory arrives, Shayne says he ensures that every piece of clothing placed on the racks for sale is in great condition.
“We spend about two to three thousand a month, depending on our load of of laundry. We get laundry every day. It never stops. It never ends,” said Shayne. “We try to we try to keep every piece as repaired as possible and as wearable as possible so that it’ll last another 30, 40, or 50 years.”
What are some of Shayne’s personal favorites hanging in the store? Western wear!
“I go a lot to other states to source those. They have crazy colors. They’re loud, they’re brash, but also they can be very quaint, and very quiet,” said Shayne with a grin. “It can also be a cool piece that you can explain to people why it’s an important piece of fashion history. A lot of people connect with it because they have uncles, or dads who used to wear them growing up.”
With three to five-thousands of pieces in stock at any time, there is always something new to discover. The demand for vintage has grown so much that Shayne decided to expand, opening a second location called Heyday by Prison City Vintage on the North Shore in Evanston.
“We get a lot of clothing and we have to find different ways to sell it, explained Shayne about opening a second location. “I started Heyday, because I had a bunch of friends who wanted to do a store, and so why not do it with them?”
At its core, Prison City Vintage is about self-expression.
“Prison City Vintage is all about having fun. It’s all about being yourself and being an individual.” explained Shayne. “If somebody wants to come in and just sit here, that works for me. As long as they want to hang out and tell friends about our store, we’re happy to have them.”
Shayne is not only committed to selling vintage fashions that makes his customers happy, he also wants to help the environment.
“Prison City Vintage matters because we’re sustainable business. We care a lot about the clothing that goes in here, and we’re saving another piece from a landfill every time we sell it. It’s really important that we use the clothing that we already have for generations ahead of us.”
A vintage playbook
Shayne believes the secret to success in retail needs to be more than strategy. He says retail needs to be a part of your soul.
“The advice I have for anybody going into retail and starting their own business is to do what you love, because that will fuel your fire,” stated Shayne with and energetic tone. “We need more passionate people in retail. People that love what they sell, people that love making connections.
“We live in a world where a lot of people are corporate, soulless, and they don’t know what they want to do. So, do what you love. It will fuel the fire for the rest of your life.”
From the customers who come in to shop, to the people who just want hang out and soak up the Prison City Vintage vibe, Shayne believes he has found his tribe.
“I love watching my customers connect with everything that we picked out here.” said Shayne with pride. “I’ve always wanted to be down here. It was always my dream and my goal to make it here in my hometown as a spot where young people could go and shop for their clothing or even just hang out.”
