Jennifer Kelly, owner and manager of Vintage Frills, has been immersed in retail since childhood. Growing up in a small Roseland resale store where her mother worked, she got her first job as a teenage cashier in a family-run thrift shop. From there, she climbed the retail ladder—first in fast fashion at Old Navy and Forever 21, then discovering her love for luxury at Coach, which led to roles at CHANEL, Neiman Marcus, Saks Fifth Avenue, GUCCI, and Tiffany & Co. But after years in luxury, she realized the industry’s glass ceiling wasn’t for her.

In 2020, 70% of Uber staff was laid off via email and Zoom, including Jennifer. She spent her quarantine time creating a business plan for Vintage Frills. That moment pushed her back to what she loved—retail, but this time on her own terms. What started as a mobile shop (a pink school bus named The Vintage Fleet) became a brick-and-mortar store when she found a vacant space on N. Milwaukee—already divided into cubbies, just like in her business plan. Since then, Vintage Frills has won Best New Retro Shop by Chicago Magazine in 2022, and Jennifer continues to use her deep retail experience to create an exciting, nostalgia-filled shopping experience that keeps customers coming back.