Where to Shop Chicago: Our favourite Second City stores
By Sara Radin

Sara Radin, WGSN Associate Editor for City By City, picks the top ten stores in Chicago. Get to know them now and tell your friends.

May 10, 2016

9 photos

Each year at WGSN, we identify emerging cities on our radar through our Style Cities report.

For 2016, we dubbed Chicago as the fashion capital of the Midwest. While the main shopping area is located in and around Michigan Avenue, we were most drawn to the independent boutique scene in smaller, emerging neighbourhoods Wicker Park, Bucktown, Logan Square and Pilsen.

Here’s a round up of the best boutiques in Chicago:



2008 North Damen Avenue / 1 872 802 4408

Neighbourhood: Bucktown

Curated by owner Catherine Becker, this concept shop focuses on Nordic and Japanese fashion and interior goods by emerging artists and designers.



2108 North Damen Avenue / 1 773 278 6150

Neighbourhood: Bucktown

Robin Richman stocks minimalist, one of a kind pieces by under the radar designers from all over the world.



2627 North Kedzie Avenue / 1 312 852 6012

Neighbourhood: Logan Square

While this high-end menswear and lifestyle shop sells well-known labels including Common Projects, Engineered Garments and Stone Island, it still has a unique point of view.



1152 West 18th Street

Neighbourhood: Pilsen

Stop into Verdant Matter for some affordable plants as well as delightful ceramics, home goods and accessories.



1346 West 18th Street / 1 312 929 2441

Neighbourhood: Pilsen

Very Best Vintage quite literally carries some of Chicago’s very best vintage; here you will find women’s apparel, footwear and accessories dating back to the 1950s up to the 1990s.



1323 N Milwaukee Avenue / 1 773 252 6996

Neighbourhood: Wicker Park

Kokorokoko’s store space is as colourful as the trend-centric and iconic ‘80s and ‘90s merchandise it carries.



1913 West Division Street / 1 773 395 2351

Neighourhood: Wicker Park

Penelope’s is Chicago’s go-to boutique for small European brands. Owned by a husband and wife duo, the store stocks quality garments with a focus on comfortable yet elevated style.


1250 N Milwaukee Avenue / 1 773 227 7743

Neighbourhood: Wicker Park

Shop an elevated selection of sneakers including limited edition exclusives.



1528 N Milwaukee Avenue / 1 773 276 7002

Neighbourhood: Wicker Park

This hip boutique carries contemporary brands as well as vintage clothing ideal for young men and juniors. Be sure to catch the sale room on the second floor and the vintage merchandise in the basement.



1911 West Division Street / 1 773 227 3180

Neighbourhood: Wicker Park

Here you will find rare, modern home goods and gifts you won’t find at larger commercial stores.

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ALWAYS TRAVELLING? Discover must-see stores, as well as the best hotels and restaurants with our incredible City-By-City guides.

  • Nice list! Damen/Wicker Park has that grubby-chic blend of artist studios, independent book stores, good coffee, plus the amazing-iconic Reckless Records and a louche womens boutique Eskell…

  • Got to check out “Scout” in Andersonville!! Urban antique shop that takes familiar elements – simple and unadorned – and makes them feel interesting and sophisticated again.

  • Check out designer boutique Anastasia in Chicago!

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