Remember when an afternoon on Southport meant wandering into little boutiques you couldn’t find just anywhere? Before today’s familiar national storefronts, independent shop owners and specialty retailers helped shape the avenue’s distinctive personality.
Our archives preserve early images of shops that residents still mention with affection. This installment of our 15-year anniversary series looks back at the storefronts that made discovery part of a walk down Southport.
Perchance: Part of the early shopping landscape
Perchance is one of the most recognizable names in the early Southport photo archive. The storefront and its eventual for-lease sign captured an era of small, individually curated shops.
M2: Personality on the avenue
M2 brought gifts, accessories and boutique finds to the corridor for years. Its owners reported losing their lease in 2021, and the shop closed that October. The reaction from customers showed how much a small store can mean to its regulars.
Cerato: Independent style
Cerato at 3451 N. Southport was known for clothing and an emphasis on local Chicago designers. Its independent point of view was representative of what made the shopping street stand out.
She One and the storefronts people remember
She One was another name that appeared in early neighborhood photo tours. Readers also remember Two Penny Blue, Princess Club, Click Shoes and More, Que Syrah and Spencer’s Jolly Posh Foods—each with its own personality and place in Southport’s evolving history.
Mint Julep and other independents
Mint Julep, formerly at 3432 N. Southport, is another boutique people remember from the older retail mix. Children’s retailer The Red Balloon Company and outdoor favorite Uncle Dan’s/Gearhead also became part of the neighborhood’s changing storefront story.
What changed?
Southport’s popularity attracted larger retailers, greater investment and renewed interest in commercial space. But higher rents and changing leases created challenges for smaller shops. The transformation wasn’t simply about the arrival of brands: it was also about losing some of the individuality that brought people here.
Not every independent disappeared. Longstanding local businesses continue to give the corridor character, and new independent concepts still deserve community support.
Tell us which shop you miss
Which former Southport boutique do you wish you could walk into one more time? Perchance? M2? Cerato? She One? Or another favorite? Tell us below—and share old photos if you’ve got them.
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