Gemini & Penelope's

Jena Frey and Joe Lauer are collectors. Their first store, Penelope’s, began as an idea to sell the clothes and vintage furniture they had collected from years of Midwest road trips. The furniture portion of the store was born of necessity in that they were quickly running out of space. The clothing, on the other hand, happened because they were young enough to take a risk. “We didn’t have any worries,” Jena says. “There was no ‘what if we do this and fail,’ we just thought, ‘oh! We can do this, right? This is no big deal!’” At the time, competition was low, making a “Mom-and-Pop shop” in Wicker Park all the more desirable. Always ahead of the curve, Jena and Joe opened Penelope’s before the neighborhood became inundated with similarly-styled boutique stores. “There were a lot of art galleries and similar things on Milwaukee [Avenue],” Jena explains. “It seemed like a lot of creative things were happening in this neighborhood in the early 2000s.” The clothing labels and collections they most loved throughout their travels had been primarily selling to small boutiques; so, taking a cue from artistic neighbors with a unique interest in smaller brands, Jena and Joe jumped at the opportunity to be the first to sell to that market. Nearly two decades later, they aren't selling furniture anymore, but they have expanded their clothing sales to a sister shop right next door called Gemini, and the neighborhood is as vibrant and bustling with life as ever.

While many of those early labels they fell in love with have since folded, the thrill of the hunt for new brands keeps the dynamic duo going, especially when it comes to international styles. Jena beams as she talks about their more recent acquisition of Spanish-designed clothing. “For a long time we had French brands,” she says, “and a lot of American brands. But every country has its own vibe, and it’s great to get a taste of that.” There is certainly something about the way the stores are organized that they feel like a tasting menu for fashion enthusiasts, and this has only grown with the expansion to Gemini. “We’d always carried a lot in that very little space [in Penelope’s],” Joe explains, comparing their pre-Gemini backstock to that of a major department store. “Men’s, women’s, shoes, accessories, self-care products, home goods; we’ve always done a lot over there, and we wanted to expand into kids, and a lot of our brand partners began expanding as well.” But it would be several years before their dreams of expansion would come true. After all, they were new parents, and still figuring out the trick of co-owning a store which demanded their attention while maintaining a healthy work-life balance at home (the trick, it turns out, is to keep the schedules flexible and fair, with room for adjustment, so that both parents can still take time to be with the family).

     They knew that when they finally expanded they didn’t want to leave the neighborhood, let alone their perfect little block on Division, so when the space next door became available for lease, it was a kind of kismet. Jena and Joe set to work opening Gemini, splitting up the stock in a manner that gives the sense that Penelope’s is the original, classic store with an array of fashion and accessories for all ages, while Gemini gets to be the fashionable “mature” sister, with clothing and designs tailored to a slightly older crowd.

There is one thread throughout the Penelope’s journey. It’s something that fueled the conversation with Jena and Joe, and snuck up in places you wouldn’t expect: a deep devotion to community. Olive Well talks about community a lot, it’s a staple in our profiles of neighborhood businesses. But for Jena and Joe, the Wicker Park community is their raison d’être. Not only did neighbors inspire the boutique label focus, but neighborhood children would eventually grow up to work at Penelope’s and Gemini; as those neighbors had children of their own, it inspired growing the business to accommodate them. Even subtle community-related aspects, such as double-wide sidewalks for strollers and families, played a major part in the decision to open the shops on West Division Street.

For under-the-radar brands that’ll make you look stylish all year long, and are sustainably and responsibly made, Jena and Joe recommend Paloma Wool and Rita Row. Both from Spain, these brands are extremely transparent about their process, staying fun and colorful while continuing to be eco-friendly with accessible pricing. Another label Joe recommends is 7115, based in Manhattan, it’s a collection heavily inspired by Scandanavian minimalism, for those days when you want to feel chic and simple.

Photography by Alina Tsvor

Text by Eric Grant

1643 N Milwaukee 

Chicago, IL

Tel 773.480.5078

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OLIVE WELL IS A TEAM OF REAL ESTATE AGENTS AFFILIATED WITH COMPASS, A LICENSED REAL ESTATE BROKER WITH A PRINCIPAL OFFICE IN CHICAGO, IL, AND ABIDES BY ALL APPLICABLE EQUAL HOUSING OPPORTUNITY LAWS. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATIONAL PURPOSES ONLY. INFORMATION IS COMPILED FROM SOURCES DEEMED RELIABLE BUT IS SUBJECT TO ERRORS, OMISSIONS, CHANGES IN PRICE, CONDITION, SALE, OR WITHDRAWAL WITHOUT NOTICE. NO STATEMENT IS MADE AS TO ACCURACY OF ANY DESCRIPTION. ALL MEASUREMENTS AND SQUARE FOOTAGES ARE APPROXIMATE. THIS IS NOT INTENDED TO SOLICIT PROPERTY ALREADY LISTED. NOTHING HEREIN SHALL BE CONSTRUED AS LEGAL, ACCOUNTING OR OTHER PROFESSIONAL ADVICE OUTSIDE THE REALM OF REAL ESTATE BROKERAGE.