In addition to the shops below, see individual listings here:

Alamo Shoes:
This old-school Andersonville shoe store (clerks help you try them on) is a little bit granola and only sells shoes that are actually comfortable. Expect an array of Keens, Birkenstocks, and Clarks. 5321 N. Clark St. tel. 773/784-8936. El: Red Line to Berwyn. 

Barneys Warehouse: For bargains, head to Barneys Warehouse at the Fashion Outlets of Chicago, near O’Hare in Rosemont at 5220 Fashion Outlets Way; El: Blue Line to Rosemont 

Florodora: Old-meets-new at this women’s boutique in the Loop, which sells contemporary clothing based on vintage looks. The shop is in a historic building, which adds to the vibe. 330 S. Dearborn St. (at Van Buren St.). tel. 312/212-8860. El: Blue Line to Monroe. 

Fluevog: The styles at this shoe store are a little bit elfin, a little bit rockabilly, and a lot intriguing. The Wicker Park shop has options for women and men, and runs decent sales. 1539 N. Milwaukee Ave. (near North Ave.). tel. 773/772-1983. El: Blue Line to Damen. 

Hazel: The women’s selections are a bit flirty and men’s are quite dapper at this reasonably priced boutique in Ravenswood. Talented buyers bring in fun finds from around the world. For accessories, there’s a shop by the same name about a block east. 1926 W. Montrose Ave. tel. 773/904-7779. Brown line to Montrose. 

Hermès Chicago: Hermès makes the world’s most sought-after scarves and ties. Don’t be intimidated; even if you’re not buying, it’s fun to walk through and gaze at the colorful designs that earned these silk accessories a cult following. 25 E. Oak St. tel. 312/787-8175. El: Red Line to Chicago. 

Kate Spade: Head here for designer handbags, ranging in style from plaid and gingham to snakeskin and basic black. The shoes and stationery goods are adorable, too. 56 E. Oak St. tel. 312/654-8853. El: Red Line to Chicago. 

McShane’s Exchange: This Lincoln Park consignment shop sells designer clothes at real-person prices. Sorry guys: They carry only women’s clothing. 815 W. Armitage Ave. tel. 773/525-0282. El: Brown Line to Armitage. 

Optimo: “Dashing” is an understatement for the hats made at this shop in the Loop, the name of which is uttered with reverence by fashion hounds. Those purchasing custom felt and straw hats are interviewed and measured, and hats are created for their noggins alone. 51 W. Jackson Blvd. (at Dearborn St.). tel. 312/922-2999. El: Blue Line to Monroe. 

p45: Of the cool boutiques aimed at the well-heeled crowd clustered along Damen Avenue in Bucktown, this is among the more daring. The urbane women’s fashion is funky rather than girly, and carries a mix of new and known designers, with clothing, shoes, and accessories. 1643 N. Damen Ave. tel. 773/862-4523. El: Blue Line to Damen. 

Prada: A boutique so chic it’s almost painful. Chicago’s top spot for buying the famous Italian designer’s signature bags. 30 E. Oak St. tel. 312/951-1113. El: Red Line to Chicago. 

Scotch and Soda: This Amsterdam-based brand brings Euro fashion to Wicker Park for men and women. Styles range from simple and conservative to bright, pattern-filled conversation pieces. 1639 N. Damen Ave. tel. 773/687-8980. El: Blue Line to Damen. 

Stock MFG: No more baggy khaki’s and puffy shirts. This West Loop men’s store sells quality, locally made clothes that fit. 2136 W. Fulton St. tel. 312/371-1555. El: Green Line to Ashland. 

Swaby: Shernett Swaby, a finalist on Project Runway, sells her boundary-pushing designs at her River North shop. It’s not cheap, but you know you’ll never run into someone else dressed alike. 750 N. Franklin St. (at Chicago Ave.). tel. 312/285-2810. El: Red Line to Chicago.  

T-Shirt Deli: The staff here serves up customized T-shirts while you wait. Come up with your own message, or browse the pre-made offerings, rich in Chicago themes. Just like at a real deli, your purchase is wrapped in white paper and served with a bag of potato chips. There’s also a location in Andersonville. Bucktown: 1739 N. Damen Ave. tel. 773/276-6266; Andersonville: 1482 W. Berwyn Ave. tel. 773/561-7410. El: Blue Line to Damen; Red Line to Berwyn. 

Zara: Euro chic clothing, shoes, and accessories from the Spanish mass merchandiser have taken Michigan Avenue by storm at this Chicago flagship. You’ll find three floors of classic pieces with an edge, as well as the trendiest items from across the Atlantic, all at extremely reasonable prices. 700 N. Michigan Ave. tel. 312/255-8123. El: Red Line to Chicago. 


Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.