From luxury to local: Jennifer Kelly’s journey to Vintage Frills

In 2020, Jennifer Kelly rolled a bubble-gum-pink school bus onto a street in Chicago and opened its doors to racks of vintage dresses and glittering costume jewelry. The mobile boutique — nicknamed “The Vintage Fleet” — turned heads long before she had a permanent storefront.

Kelly didn’t know it then, but that bus would carry her into an award-winning business.

“I was scared to take a true leap,” she said. “The bus was my way of cheating.”

She had left her job as operations coordinator at Tiffany & Co. in December 2019, and less than a year later, she was laid off from Uber via email during the COVID-19 pandemic. But what could have been an ending felt more like a beginning.

“I really think it was a sign,” Kelly said. “The universe was telling me: This isn’t your forever home.”

After years climbing the luxury retail ladder — from Chanel to Gucci to Tiffany — Kelly realized she wanted to build something of her own, a business that reflected her creativity, love for fashion and desire for work-life balance.

This bus was affordable for Kelly during a slow market, letting her test her concept without the full financial risk of a storefront, and it sparked curiosity. Kelly remembers it as a pivot point. She scouted estate sales, filled her basement with finds and treated sourcing like a mission. She said once she “literally bought out the entire estate,” recalling one haul that supplied gowns and jewelry from across decades. The severance she received from Uber provided the runway to pay the first few months’ rent when a permanent space became available.

What started as a mobile trial grew into a vintage shop named Vintage Frills, a pastel-colored vintage shop that opened in 2021 on Milwaukee Avenue of Logan Square. Chicago Magazine recognized it as the city’s Best New Retro Shop in 2022. Kelly’s store now anchors a once-empty stretch of Logan Square, offering not just vintage fashion, but an experience that blends nostalgia, sustainability and community spirit.

“Vintage is luxury in its own way,” Kelly said. “So when I’m picking out things, I make sure the pieces I have in store represent that luxury, but also budget-friendly not ‘outlandish’ so even a college student can afford. My goal is to continue to educate and show quality garments.”

When Kelly moved in, Milwaukee was nearly empty. Vacant storefronts lined the street, and few shoppers passed by. But she was soon welcomed by nearby minority business owners like Hispanic co-founder of Monarch Thrift Shop Mireya Fouché, who offered guidance and encouragement. That early sense of community stayed with her.

Today, Kelly serves as vice president of the Logan Square Chamber of Commerce, helping support other local entrepreneurs while keeping her store involved in neighborhood events.

“Vintage Frills is amazing,” said Nilda Esparza, the chamber’s executive director. “They’re very creative. They put on some of the most creative fashion shows I’ve seen. Our thrift stores and our secondhand consignment shops are becoming more and more eclectic here in Logan Square.”

Kelly’s team regularly stages themed fashion shows—from “Sex and the City” to “Harry Potter,” and often collaborates with local markets and community events.

“Chicago has fashion, too,” Kelly said. “I want people to see that you don’t have to go to New York or L.A. to have fun with style.”

Liam Bermejo, 22, who recently joined the staff after modeling in Kelly’s Sex and the City-themed fashion show, enjoyed his five days so far with this store. Now, he helps with styling and merchandising.

“This is such a great environment, such an amazing concept and project that Jen has created here, all this has come from her imagination,” Bermejo said. “She has such an amazing spirit and personality. She’s never been sad or mad. I try to emulate that in my life entirely.”

At Vintage Frills, Kelly has built not just a store but an experience. Each “cubby” in the shop is color-coded and designed as a mini-world of its own — lavender rooms filled with vintage blouses, sunshine-yellow corners stacked with retro handbags. Kelly designed every display herself and even trademarked the color-coordinated layout.

Brittany Weber, a customer who has visited Vintage Frills several times, said she bought a few different guest wedding dresses. One of her favorite finds was a coral pink satin dress from the 1960s, long-sleeved and elegant, while another was a green cotton gown from the 1970s decorated with crocheted flowers.

“They have a good variety of clothes, and I like their location and the prices are pretty good,” Weber said. “I’ve had a very positive experience every time I’ve been here.”