Within a few months of launching The Signature Fit, a women’s fashion brand based out of Chicago, Kiara Lee and Darnyá Jamerson attended a large fashion trade show in Las Vegas.

Looking back, they realized the chance to connect with other entrepreneurs helped jumpstart their small business.

“There were hundreds and hundreds of vendors there,” Lee said, at a time when the fashion-loving pair – who met as students at the University of Illinois at Champaign-Urbana – were trying to figure out their business identity. “We were able to network and get all the contact information, to ask other business owners what products that they had.”

Lee and Jamerson ended up pivoting their business model from the original concept of women’s workwear to more versatile, multi-purpose clothing: think matching loungewear sets, joggers and maxi dresses, often in breathable, stretchy fabric. Given the impact of COVID-19 and the surge in people working from home, “We wanted to have the outfits people can wear and lounge in at home, or not,” Lee said. “So every piece that we have, you can either dress it up or down.”

At a time when COVID-19 is still rippling through many parts of the country, inflation is peaking, and supply chain issues loom large, owners of independently-owned companies like Lee and Jamerson say they are eager to connect with others facing less-than-ideal market conditions. They’ll be among 30 Black-owned businesses seeking tips, tricks and mutual relief at the The Thank You Chicago Juneteenth Market, a pop-up market that organizers say they created to foster a Black-owned small business community.

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Hosted at The Promontory music and events space in Hyde Park on June 19, the date of the Juneteenth holiday commemorating the end of slavery in the United States, the pop-up is geared toward fashion, food and skin care. The event is free and open to the public; attendees can browse the vendors’ offerings, plus listen to music from DJ Fresh Da Juice and DJ Mustafa Rocks while shopping. 

Co-organizer K Moon said organizers were inspired to put on the first edition of the event in June 2021, when Juneteenth became a federal holiday. “We felt it was just our duty to add to that celebration by creating an event and an atmosphere where people can all come together and be supportive of one another.”

Moon was inspired by the concept of farmers’ markets, where vendors mix and mingle with each other and shoppers. “With these small businesses, a lot of them are creating their products within their homes. So, their products are like their babies.”

The Signature Fit will be one of the vendors selling there. Typically, Lee said, The Signature Fit does much of its business online, aided by social media promotion. An ambassador program they started on social media drives interest. Jamerson said that, as of June 2022, around 1,300 content creators work to promote the brand on social media. The creators get discounts and a 10% commission on every sale they make through a unique referral link they share with their followers. “Our dream one day is to have a huge team working behind us, and maybe even an office building where we have a space specifically for The Signature Fit,” Lee said of her business, which is currently run out of a storage unit.

Pop-ups and other opportunities for small businesses are important ways to meet people in-person. The pop-up, Jamerson said, “gives people in the area who have heard about us who have shopped online to get the opportunity to see everything in real life. They can see and touch the clothing.”

Since establishing The Signature Fit, Lee and Jamerson have been working on expanding merchandise and adding to their team. The brand has adopted inclusive sizing, now offering sizes from extra-small to triple extra-large. They have hired a virtual assistant and a fashion assistant to their organization, and are at work on a new line of denim, which Lee and Jamerson estimate will be available in the fall of 2022. These efforts have been reflected in the organization’s profits, which are still under $50,000 but doubled from 2020 to 2021.

The pair still look to other, more established fashion designers for ideas. Lee in particular draws inspiration from fashion designer Nichole Lynel, whom she discovered on Instagram and whose designs sell at high-end stores like Nordstrom. “She’s also a Black woman who started a boutique from nothing,” Lee said. “And now she’s styling celebrities and so many other people. And her denim is definitely her staple piece that brought her out.”

That sort of success story looms large for Jamerson and Lee, who still are in start-up mode and juggle multiple roles in the business. Jamerson manages the inventory, and shoots and edits photos for the website and social media. Lee manages The Signature Fit’s social media accounts and communications with their brand ambassadors. “There are so many moving parts,” Jamerson said.

Inflation and supply chain issues are adding extra strain, but where some small business owners worry, these designers remain optimistic. “It almost feels like a good thing that we’re starting off this way, in such a difficult time with the economy right now,” Lee said. “I feel like once we overcome this we can go through anything, we’ll be ready for anything. And that’s just gonna make our business stronger in the long run.”

If you go: The Thank You Chicago Juneteenth Market takes place on June 19 at The Promontory (5311 S. Lake Park Ave. West in Chicago) from 2 p.m. to 7 p.m. Admission is free, and 30 vendors will have products for sale.

Isabella DeLeo is a freelance writer based in Chicago. For more free things to do this summer, check out WBEZ’s Free Summer Guide.