City: Chicago, IL

Category: Shopping

Telephone: (773) 278-6150

Address: 2108 N. Damen Ave.

Description: In an interior that could be described as rustically romantic, fashion maven and School of the Art Institute grad Robin Richman sells the stuff she loves. And it has been the model for her success since she opened her Bucktown store nearly a dozen years ago. Interspersed on antique French tables and Lucite shelves, under glass cake covers and complemented by metal skirt forms, she displays an internationally diverse collection of designers. Everything from artistic shoes to vintage-styled hats and mittens to drapy menswear-inspired women’s clothing and leather-focused jewelry. Open Tues through Sun; closed Mon (open Mon in summer).

City: Chicago, IL

Category: Shopping

Telephone: (312) 640-0878

Address: 72 E. Oak St.

Insider Pick:

Description: Originally opened in a Gold Coast office building, Sofia struck a chord with fashion-conscious Chicagoans looking for that perfect mix of vintage and couture. So local sister act Ashley Zisook and Allison Zisook Goldstein moved to swanky Oak Street digs down the street from Prada, Wolford, and Hermès. Though their address has changed, they have not given up their motto of encouraging clients to “live lovely.” Named in honor of the inimitable Sophia Loren, Sofia now carries a selection of emerging designers and classic favorites: color-dyed M2F Denim shorts, cardigans from the Winter Kate line from Nicole Richie (look for her signature in one of the dressing rooms), and Chanel dog tags and handbags. Select vintage pieces round out the effortlessly chic look. Open daily.

City: Chicago, IL

Category: Shopping

Telephone: (773) 396-7979

Address: 1167 W. 19th St.

Description: Three friends plus an empty bedroom (thanks to a breakup with a boyfriend), plus a whole bunch of vintage clothing, equaled a big idea for Christine Bejasa, Alysse Dalessandro, and Kirsten Kilponen. They decided to open a shop (Bejasa has since moved to New York and has a branch there too). It’s open, you guessed it, sometimes, and it changes locations pretty frequently too, but it’s always a limited selection that’s always super-affordable. Just sign up for their e-mails and find out when they’re ready for another sale. If you love yarns of yesteryear from the 1940s through ‘90s, you’ll be happy you did.

City: Chicago, IL

Category: Shopping

Telephone: (773) 292-4123

Address: 2556 W. Chicago Ave.

Description: Lesley Timpe’s time studying fashion in Spain gives her line of women’s clothing and accessories a certain European touch. She began her Chicago business by selling to other boutiques, but realized her own dream when she opened her Ukrainian Village boutique in 2010. She focuses on natural and organic fabrics and vintage prints in her hand-crafted dresses, blouses, handbags, headbands, and her signature sassy reversible sewn hats that run the gamut from traditional black herringbone to funky faux fur–lined. She also carries pieces by other designers such as Megan Lee Designs and jewelry by Scarlett Garnet and Veronica Riley Martens. Open Wed through Sun; Mon and Tues by appointment.

City: Chicago, IL

Category: Shopping

Address: 3011 N. Broadway

City: Chicago, IL

Category: Shopping

Telephone: (866) 300-7713

Address: 1035 W. Madison St.

Description: This West Loop shop is perfect for those “find-it-for-less” kinds of wardrobes. Kim Hiley scours the coasts for the best on-trend, of-the-moment fashions that keep comfort in mind and brings them back here. Like tunic dresses from Orion London, sassy going-out tops from Tracy Reese, and dresses by Susana Monaco. Find the perfect office-to-night-out outfits, feminine summer shirts that give you that effortlessly L.A. look, and winter-warm sweaters that keep you fashionable through the frost. Open daily.

City: Chicago, IL

Category: Shopping

Telephone: (773) 698-8162

Address: 1744 W. Division St.

Description: The simple and lovely trillium flower gets translated into this minimalist space with dark hardwood flooring and a spotlight on the weekly-changing selection of boyish girly clothes, accessories, and shoes. Owner Erica Cook focuses on designers like Steven Alan, Joie, Twinkle by Wenlan, and Billy Reid who offer easy ways to layer, like bright striped tanks or flirty dresses under flouncy cardis, or colorful Swedish Hasbeens high-heeled clogs with a simple, sophisticated pair of jeans. Open Tues through Sun; closed Mon.

City: Chicago, IL

Category: Shopping

Telephone: (773) 549-2876

Address: 3738 N. Southport Ave.

Insider Pick:

Description: When Tula owner Laura Westgate announced in August 2010 that her then 4-year-old Southport shopping corridor boutique would close due to the down economy, there was such a universal cry from customers to keep it open that she reconsidered. Instead, she broadened her price points and cut back a bit on store hours. Thanks to loyal supporters, you can still visit this charming hidden-away spot for timelessly beautiful wardrobe pieces like a luscious cardigan from L.A.-based Pete, and a flowery chiffon top from Hanii Y. Open Tues through Sun; closed Mon.

City: Chicago, IL

Category: Shopping

Telephone: (773) 772-7429

Address: 2048 N. Damen Ave.

Description: The service: welcoming, customer-focused, funny. The clothes: impeccable, flattering, on-trend, and curve-friendly. Yes, this Bucktown boutique caters to women sizes 12 to 24 and does so with respect and understanding. Owner Stephanie Sack serves as a stunning model for her picks from designers including Comfy USA, Zen Knits, and Kiyonna. In here, size really doesn’t matter; it’s all about style. Open daily.

City: Chicago, IL

Category: Shopping

Telephone: (312) 226-9000

Address: 818 W. 18th St.

Description: With studio in the back and organically minded retail space up front (check out hand-made old-growth wood display pieces), local designer Annie Novotny’s Workshop is a perpetual work in progress. Her sustainable sensibility translates to a unique aesthetic—for example, she’s been inspired by colors and patterns from the photographs of rural farmers from the Depression—and feminine, floaty flair that has an equally modern mind. Her School of the Art Institute background means she has a certain giddiness about accessories like buttons made out of her vintage fabric scraps and one-of-a-kind jewelry by local arty friends. Although she sells to retailers around the country, all of her items are sewn in Chicago by workers who receive a fair and living wage. Open Wed through Sun.

City: Chicago, IL

Category: Shopping

Telephone: (773) 395-2999

Address: 1804 N. Damen Ave.

Description: Some of today’s designers like Paul Smith, Phillip Lim, Earnest Sewn, Rag & Bone, and Band of Outsiders give young, style-­conscious guys just the right not-trying-too-hard good looks. Opened by sister team Sarah and Amy Blessing, their Bucktown shop carries them all and achieves a surprisingly manly physique with its concrete floors and rustic wood accents. It also carries accessories, including casual-day cufflinks, grownup jeans, sunglasses, and messenger bags. Open Tues through Sun; closed Mon.

City: Chicago, IL

Category: Shopping

Telephone: (773) 549-1038

Address: 855 W. Belmont Ave.

Description: When the logo is a silhouette of a leggy woman holding a machine gun of some kind, you know this is not your average store. And since its opening about 15 years ago, it has not and never will be average. Among its 5 floors and 10,000 square feet, you’ll find an eclectic mix: earthy leather Timberland boots, Chrome messenger bags, true army surplus on the 3rd floor (top floor is vintage), skater-friendly sneaks, goofy adult-sized feetie pajamas, and Goth-geek unicorn corpse pendants. Don’t let the shaggy staff and no-frills atmosphere fool you: This is not inexpensive stuff, but it’s likely hard to find anywhere else. Open daily.

Name: no value!

City: Chicago, IL

Category: Shopping

Insider Pick:

Description: Recently expanded, this Boystown shop is named (backward) for owner Marc Engel who first opened the high-end Chasalla on Oak Street. He has created a casual-yet-cool look—a chalkboard wall, metal pipes used as racks, repurposed dressers for tables, and a couple of old wood Pepsi boxes to hold accessories. Designers are both American and European (Diesel, Ben Sherman, G-Star, Cheap Monday, Penguin, Lacoste), with a variety of both budget-friendly and happy splurges. There is a selection of women’s wear too. Open daily.

City: Chicago, IL

Category: Shopping

Telephone: (773) 477-1737

Address: 3331 N. Broadway

Insider Pick:

Description: Recently expanded, this Boystown shop is named (backward) for owner Marc Engel who first opened the high-end Chasalla on Oak Street. He has created a casual-yet-cool look—a chalkboard wall, metal pipes used as racks, repurposed dressers for tables, and a couple of old wood Pepsi boxes to hold accessories. Designers are both American and European (Diesel, Ben Sherman, G-Star, Cheap Monday, Penguin, Lacoste), with a variety of both budget-friendly and happy splurges. There is a selection of women’s wear too. Open daily.

City: Chicago, IL

Category: Shopping

Description: On his blog, Haberdash owner Adam Beltzman features both a romantically in-depth history of jeans and a glossary of denim-related terms. You see, Beltzman, a former lawyer, is a thinking-man’s style-guider. He thinks gym clothes belong in the gym, and he uses the words “dapper” and “gentleman” without pause. But far from being stuffy, this Old Town boutique is woody-warm and welcoming, featuring blazers, comfortable work shirts, slacks, wool pullovers and chunky cardigans, and solid leather shoes meant to look sharp and last long. Another slightly hipper, younger brother store is in River North at 607 N. State St. (312-642-8551). Open daily.