16. Cerato Boutique
City: Chicago, IL
Category: Shopping
Telephone: (773) 248-8604
Address: 3451 N. Southport Ave.
Description: Unabashedly Chicago-centric and fearlessly feminine, this Southport shop is named for a Bach flower remedy (Dr. Edward Bach created a series of flower-based homeopathic dilutions, each with a different purpose). Cerato is said to boost confidence in your inner voice and intuition. With total confidence in the abilities of local designers, Cerato looks right here for its offerings. From Avery Layne’s mod-ish dresses to Brynn Capella’s Italian leather handbags to Elise Bergman’s sweet-sexy collection of handmade pieces and the costume-jewelry-turned-stunning statement accessories by Jen Cook. Forget following the crowd, Cerato makes it trendy to be yourself. Open daily.
17. Dovetail
City: Chicago, IL
Category: Shopping
Telephone: (312) 243-3100
Address: 1452 W. Chicago Ave.
Description: Somethings old are transformed into somethings new at this delightful vintage boutique in West Town. Little crystal-y chandeliers and made-over grandma-type furnishings create the perfect setting for Julie Ghatan’s and Jennifer Clower’s repurposed and re-energized wardrobe pieces for men and women, plus jewelry, mid-century home furnishings, and art. Open Wed through Sun (opening usually at 1 p.m.); closed Mon and Tues.
18. The Dressing Room
City: Chicago, IL
Category: Shopping
Telephone: (773) 728-0088
Address: 4635 N. Lincoln Ave.
Description: The oft-changed windows of this petite Lincoln Square shop tempt with cute-trendy dresses, jackets, and tees. Owners and Lincoln Square locals Barbara Ruiz and Sarah Sanchez carry women’s wear that works for dames who are done with super-tight and too-short everything, but haven’t deferred to mom jeans or muumuus—and don’t feel like spending a small fortune. Find a great selection of jeans, funky tees, and fun skirts, along with Hanky Panky undies, and fleece-lined wool gloves and leggings. Be sure to check their Facebook page for seasonal specials. Open daily.
19. Embellish
City: Chicago, IL
Category: Shopping
Telephone: (773) 525-4400
Address: 4161 N. Lincoln Ave.
Description: Need to add a little pizzazz to your life? Then you need a little Embellish in your life. This cozy North Center store is an accessory-lover’s dream come true—jewelry by D-Amato, men’s wallets by Hippo Handcrafted, bags by Nino Bossi, or locally created and uniquely styled hats from Squasht. And most everything comes with a jaw-droppingly low price tag. Open daily.
20. Florodora
City: Chicago, IL
Category: Shopping
Telephone: (312) 212-8860
Address: 330 S. Dearborn St.
Description: You might not expect to find a super-cute independently owned boutique right in the Loop. But there it is. When Michael Blossom opened Florodora—named for a 1900 Broadway musical famous for its “Florodora Girls”—in the historic Monadnock Building in 2007, he received widespread applause from style-conscious women around town. It has remained a go-to spot for dresses, vintage-inspired coats, romantic summer frocks and flirty skirts. Since prices lean to the steeper side, be sure to keep the store’s semiannual “Scandal Sale” on your radar. Open Mon through Sat; closed Sun. Florodora Shoes too, 348 S. Dearborn St.
21. Handle With Care
City: Chicago, IL
Category: Shopping
Telephone: (312) 751-2929
Address: 1706 N. Wells St.
Description: Just as there are two sides to every story, there are two sides to this longtime Old Town boutique: One is designer-casual with loftlike decor, the other, designer-dressy with a fancier feel. Both are rather designer-priced, if you know what we mean. But it’s the select pieces from names like Rebecca Taylor, Trina Turk, Shoshanna, and alice + olivia that have made for loyal customers since the shop opened in 1981. Open daily.
22. Ikram
City: Chicago, IL
Category: Shopping
Telephone: (312) 587-1000
Address: 15 E. Huron St.
Description: Although Ikram Goldman’s stunning haute-couture boutique was a standout from its start, when word got out that one Michelle Obama entrusted Ikram with outfitting her, fashionistas everywhere took note. And while Goldman never speaks of her fashionable friendship with the First Lady, Chicago is certainly proud of the connection. It’s an understandable one, too, what with names like Jean Paul Gaultier, Rodarte, Givenchy, Yohji Yamamoto, and Sonia Rykiel gracing her sophisticated shop. Goldman also carries one of her purportedly personal favorites for the high-society set, Jimmy Choos. The shop recently moved from Rush Street into this much larger space.
23. Knee Deep Vintage
City: Chicago, IL
Category: Shopping
Telephone: (312) 850-2510
Address: 1425 W. 18th St.
Description: This Pilsen shop isn’t about second-hand. It’s vintage. And it is not trash. On the contrary, it’s most definitely treasure. In the form of wearable old T-shirts from the 1950s or 1980s, cashmere sweaters, authentic navy jackets, and a fabulous assortment of shoes that add a bit of “cool” to any outfit. The great thing, too, is that it’s not a sprawling store that sucks the energy out of your shopping hunt; it’s meticulously organized with salespeople who are genuinely excited about helping you find your treasure. Open daily (generally starting at noon).
24. Krista K
City: Chicago, IL
Category: Shopping
Telephone: (773) 248-1967
Address: 3458 N. Southport Ave.
Description: In 2002, Krista Kaur Meyers carved out a sizeable niche for herself on Chicago’s trendy Southport Avenue shopping strip. It didn’t take long for Krista K to add more space and then expand with Krista K Maternity a half-block north (3530 N. Southport Ave.). The attraction? An entire floor dedicated to top-end denim from the likes of Splendid, James Jeans, and Paige Denim; and a separate top floor selection that includes finds like a drape dress by Haute Hippie, a flowy pleated polyester blouse by Elizabeth and James, or open-toe high-heel suede booties by Pedro Garcia, made in Spain. Open daily.
City: Chicago, IL
Category: Shopping
Address: 1872 N. Damen Ave.
26. Ms. Catwalk
City: Chicago, IL
Category: Shopping
Telephone: (773) 235-2750
Address: 2042 N. Damen Ave.
Description: At this candy-stripe-painted Bucktown shop, you can pick up a little something for a strut around town without howling at the prices. Lace and ruffles, silky sleeves, puff-bottomed jackets, and a vintage-ish selection of tees all create a flirty, fun look from designers like Esley, RYU, Ya, and Fumblin Foe. Open Wed through Sun; closed Mon and Tues.
27. P+L Boutique
City: Chicago, IL
Category: Shopping
Telephone: (773) 248-3758
Address: 2956 N. Clark St.
Description: Named for husband and wife team Paul Chiemmongkoltip and Leena Thairuammit, this Lakeview shop has a motto that sets the stage: “Happywear for women and men”—and now kids too. Thoughtfully selected designs from around the world include heathered pima cotton cowl neck sweaters from Alternative Apparel, a sleeveless wraparound sweater-dress from Spain’s Skunkfunk, and hipster loafers for guys from British-based J Shoes. One glance at the prices, and you will look as happy as your clothes. Open daily.
28. Penelope's
City: Chicago, IL
Category: Shopping
Description: Another pioneering power couple, Joe Lauer and Jena Frey opened their super-cool clothing and hip housewares destination—named for their pet Pug—in 2002, when this strip of Division Street was derelict, offbeat, and bereft of fashion boutiques. Now, Penelope’s is surrounded by worthy followers, but it still stands strong, carrying coveted lines for women and men by Sessun, APC, Built by Wendy, and Dunderdon, with vintage-y and European flair and a solid in-the-know appeal. Open daily.
29. Penelope’s
City: Chicago, IL
Category: Shopping
Telephone: (773) 395-2351
Address: 1913 W. Division St.
Description: Another pioneering power couple, Joe Lauer and Jena Frey opened their super-cool clothing and hip housewares destination—named for their pet Pug—in 2002, when this strip of Division Street was derelict, offbeat, and bereft of fashion boutiques. Now, Penelope’s is surrounded by worthy followers, but it still stands strong, carrying coveted lines for women and men by Sessun, APC, Built by Wendy, and Dunderdon, with vintage-y and European flair and a solid in-the-know appeal. Open daily.
City: Chicago, IL
Category: Shopping
Address: 1643 N. Damen Ave.