Best Womenswear Boutiques in Chicago

Old Town’s Handle with Care has a long history, dating all the way back to 1981 when it opened as a gift boutique. Current owner Brinton Coxe took over the two-room store nearly a decade ago and evolved it to meet the needs of its customers, offering one of the city’s best selections of moderately priced designer luxury, as well as budget-friendly casual, everyday garments. The layout helpfully separates the expensive designer ware from the more affordable options.

Ross Kelly and Sasha Hodges opened Kokorokoko in 2009 after spending years collecting clothing, accessories, and housewares from the ’80s and ’90s. It’s filled with bright, funky, and unique vintage pieces, from retro sportswear and band t-shirts to a large selection of cowboy boots, quirky jewelry, and new designer accessories. All items are under $100 and there are many bargains to be found, so stop by the next time you’re in Wicker Park.

Unmissable with its arrestingly flamboyant red exterior, this huge, upscale boutique was opened by Ikram Goldman in 2011. Famous for dressing Michelle Obama for the inauguration in 2009, Ikram is fashion royalty in Chicago, and her boutique has unique selections of sophisticated clothing, shoes, and other accessories from American, European, and Japanese designers, as well as vintage pieces hand-picked by the lady herself. Need a break from shopping? There’s also a cafe and an art gallery inside the 16,000-square-foot store.

Also in Old Town is Adelaide, which, in spite of its name, specializes in imported European fashion and is committed to “enduring beauty, progressive vision, and timeless sophistication.” With the chic design of its store featuring elegant chandeliers and exposed brick walls, browsing its ever-evolving luxury collections of clothing, handbags, jewelry, and shoes is a wonderful shopping experience. Adelaide’s quality has been recognized by Forbes Travel Guide and Culture Mix Magazine.

Moon Voyage was opened in 2012 by Chicago-bred Susie Lee, and she describes it as “an edgy New Yorker meets a laid-back Californian.” To be found near the intersection of Milwaukee, North, and Damen in Wicker Park, Moon Voyager stocks on-trend apparel and jewelry by small- to mid-tier designers, as well as accessories, specialty lingerie, apothecary, and homeware. The staff also shares its expertise on its fashion and beauty blog, Voyager.

Squasht was founded in October 2004 by St. Louis native Lesley Timpe and opened its first shop in Ukrainian Village in 2010. As well as offering work by other independent designers, the folks at Squasht design and create their own seasonal lines of dresses, skirts, tops, tunics, headbands, and their signature reversible hats. Timpe was named “Best Local Clothing Designer” in 2013 and 2014 in the Chicago Reader’s “Best of Chicago” Readers’ Polls and is on hand to help you find what you’re looking for.